3-(3-Benzyloxy-4-nitrophenoxy)-1,3,4,5-tetrahydrobenzo[b]azepin-2-one → 3-(4-Amino-3-benzyloxyphenoxy)-1,3,4,5-tetrahydrobenzo[b]azepin-2-one

HRID 660769Notes

Reaction equation

HRID 660769 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:25]=[CH:26][C:27]=1[N+:28]([O-])=O)[O:12][CH:13]1[C:19](=[O:20])[NH:18][C:17]2[CH:21]=[CH:22][CH:23]=[CH:24][C:16]=2[CH2:15][CH2:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCOC(C)=O.CO.[Pt]=O>[NH2:28][C:27]1[CH:26]=[CH:25][C:11]([O:12][CH:13]2[C:19](=[O:20])[NH:18][C:17]3[CH:21]=[CH:22][CH:23]=[CH:24][C:16]=3[CH2:15][CH2:14]2)=[CH:10][C:9]=1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 688395523-(3-Benzyloxy-4-nitrophenoxy)-1,3,4,5-tetrahydrobenzo[b]azepin-2-one

Product 1

HCID 688390293-(4-Amino-3-benzyloxyphenoxy)-1,3,4,5-tetrahydrobenzo[b]azepin-2-one

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A solution of 3-(3-benzyloxy-4-nitrophenoxy)-1,3,4,5-tetrahydrobenzo[b]azepin-2-one (3.0 g, 7.4 mmol) in 50 mL EtOAc/MeOH (1:1) is hydrogenated at 1 atm over platinum oxide for 2.5 h. The catalyst is filtered and the filtrate evaporated to give the title compound which is used directly in the next step.

Workup

  1. filtrationThe catalyst is filtered
  2. customthe filtrate evaporated

Sources & evidence

ORD record
ord-91d5b6f6a8314889bdcdd785769c4d22
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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