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ChemicalBook CAS DataBase List 2-Amino-1-pyrroline Hydrochloride
7544-75-4

2-Amino-1-pyrroline Hydrochloride synthesis

1synthesis methods
In a 250 mL bottomed flask, ammonia was bubbled into ethanol (80 mL) that was cooled to -78° C. for 45 min. The saturated solution that was obtained was transferred to a Parr autoclave, which contained 4-chlorobutanenitrile (60 g, 580 mmol). The mixture was stirred and heated to 120° C for 16 hr. The reaction mixture was cooled and transferred to a round-bottomed flask. The solvent was removed under reduced pressure to afford a yellow solid, which was washed with diethyl ether and dried under a high vacuum to afford an off-white solid 2-Amino-1-pyrroline Hydrochloride, 19.5 g, 232 mmol, 40percent yield. 1H NMR (DMSO-d6) δ 9.22 (br s, 1H), 8.93 (br s, 1H), 7.60 (br s, 1H), 3.52 (d, J=7.2 Hz, 2H), 2.76 (d. J=8.0 Hz, 2H), 2.08-1.96 (m, 2H).
-

Yield:-

Reaction Conditions:

with ammonium chloride in ethanol at 20; for 24 h;

Steps:

1.A

Step A: Preparation of 3,4-dihydro-2H-pyrrol-5-amine hydrochloride (1:1) To a stirred solution of 3,4-dihydro-5-methoxy-2H-pyrrole (5.00 g, 50.43 mmol) in ethanol (30 mL) was added ammonium chloride (2.68 g, 50.43 mmol). The reaction mixture was stirred at room temperature for 24 h. The organic layer was then concentrated under reduced pressure to afford the title product as a white solid (6.0 g), which was used without further purification in the next step.

References:

US2010/99561,2010,A1 Location in patent:Page/Page column 19

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