6-Amino-3,4-dihydro-1(2H)-naphthalenone synthesis

9synthesis methods

Product Name:6-Amino-3,4-dihydro-1(2H)-naphthalenone
CAS Number:3470-53-9
Molecular formula:C10H11NO
Molecular Weight:161.2

3470-50-6
224 suppliers
$6.00/1g

3470-53-9
217 suppliers
$6.00/250mg

Yield:3470-53-9 60%

Reaction Conditions:

Stage #1: 6-Hydroxy-1-tetralonewith sodium hydroxide in N,N-dimethyl acetamide at 20 - 30; for 1 h;
Stage #2: with 2-Bromo-2-methylpropanamide in N,N-dimethyl acetamide at 25 - 35; for 5 h;
Stage #3: with sodium hydroxide in N,N-dimethyl acetamide at 50 - 60; for 1 h;

Steps:

Step 2

A 500-mL, 3-necked, round-bottomed flask fitted with a reflux condenser,thermometer and addition funnel and equipped with a large magnetic stirring bar wascharged with 3,4-dihydro-6-hydroxy-1(2H)-naphthalenone (10.0 g and 61.7 mmol) and N,Ndimethylacetamide(90 mL). Sodium hydroxide (7.40 g and 185 mmol) was added into theflask by temporarily removing the addition funnel, and the resulting mixture was stirred at 20-30 C for 1 h. Then, 2-bromo-2-methylpropanamide (30.7 g and 185 mmol) was addedto the reaction mixture through the addition funnel, and the resulting mixture was stirredat 25-35 C for 5 h. After the reaction period, sodium hydroxide (22.2 g and 555 mmol)was added, and the resulting mixture was stirred for 1 h with heating to 50-60 C (internaltemperature) using an oil bath. After the reaction was complete, water (90 mL) was addedby using the addition funnel, and the mixture was heated at reflux using an oil bath for 1 h(internal temperature: 85-95 C). Water (180 mL) was added to the reaction solution usingthe addition funnel, and the resulting precipitated mixture was allowed to cool slowly to20-30 C. The precipitated crystalline powder was collected by filtration with a Brucellafunnel and washed 3 times with 90 mL of water to obtain a brown crystalline powder 2(6.28 g and 60%), m.p. 128.8~131.2 C.

References:

Chen, Baiyu;Fu, Wei;Li, Jianqi;Li, Wei;Li, Xinwei;Xie, Peng;Zhang, Junjie;Zhang, Wenbo;Zhu, Mengdan [Molecules,2022,vol. 27,# 7,art. no. 2173]

7462-74-0 Synthesis