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CAS No. : | 2941-78-8 | MDL No. : | MFCD00007909 |
Formula : | C8H9NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NBUUUJWWOARGNW-UHFFFAOYSA-N |
M.W : | 151.16 | Pubchem ID : | 76255 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With copper(ll) sulfate pentahydrate; hydrogen bromide; copper; sodium bromide; sodium nitrite; In water; at 100℃; | CuSO4·5H2O (2.82 g, 11.3 mmol), NaBr(2.31 g, 22.4 mmol), and Cu turnings (1.50 g, 23.6 mmol) were boiled in 15 mL 47%-HBruntil the solution was colorless. 5-Methylanthranilic acid (5.00 g, 33.1 mmol) wasdissolved in 11.3 mL 47% aq HBr and 28 mL H2O under heating. This solution was addedat 100C to the CuBr solution. The reaction mixture was kept at 90-95 C and NaNO2(4.53 g, 65.7 mmol) in 25 mL H2O was slowly added under stirring. The precipitating acidwas filtered off with suction, washed with 10% aq HBr and re-precipitated from an alkalinesolution with conc. HCl. The crude acid was 3× recrystallized from H2O by use of charcoalto yield 4.00 g (18.6 mmol, 56%) white crystals, m. p. 137-139C (lit.10: 137.6-139C).IR: nu = 2923, 1703 (C O), 1590, 1436, 1302, 1260, 1215, 1031, 922, 817. 1H NMR: delta= 2.36 (s, 3H, CH3), 7.19 (dd, 1H, J = 2.5/8.1 Hz, 4-H), 7.57 (d, 1H, J = 8.1 Hz, 3-H),7.81 (d, 1H, J = 2.0 Hz, 6-H). 13CNMR: delta = 20.74 (CH3), 119.18, 130.04 (Cq, ar), 133.01,134.45, 134.61 (CHar), 137.42 (Cq, ar), 171.51 (C O).MS: m/z (%) = 216 (93) [M]+, 214(100) [M]+, 199 (58) [M - OH]+, 197 (56) [M - OH]+, 171 (29) [M - CO2H]+, 169 (36)[M - CO2H]+, 135 (55) [M - Br]+, 91 (48) [C7H7]+, 90 (68), 89 (64), 77 (37), 63 (40).C8H7BrO2 (215.05): calcd. C 44.68, H 3.28, Br 37.16; found C 44.67, H 3.26, Br 37.01. |
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