Acetic acid 7-benzyloxy-6-nitro-1,2,3,4-tetrahydronaphthalen-2-yl ester → Acetic acid 6-amino-7-benzyloxy-1,2,3,4-tetrahydronaphthalen-2-yl ester

HRID 643905Notes

Reaction equation

HRID 643905 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][CH:15]([O:19][C:20](=[O:22])[CH3:21])[CH2:16]2)=[CH:11][C:10]=1[N+:23]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCOC(C)=O.[Pt]>[NH2:23][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:16][CH:15]([O:19][C:20](=[O:22])[CH3:21])[CH2:14][CH2:13]2

Participants

4

Reactant 1

HCID 66750447Acetic acid 7-benzyloxy-6-nitro-1,2,3,4-tetrahydronaphthalen-2-yl ester

Product 1

HCID 66750966Acetic acid 6-amino-7-benzyloxy-1,2,3,4-tetrahydronaphthalen-2-yl ester

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of acetic acid 7-benzyloxy-6-nitro-1,2,3,4-tetrahydronaphthalen-2-yl ester (1.01 g, 2.96 mmol) and 5% Pt/C (150 mg) in EtOAc (20 mL) is hydrogenated at 1 atm and at ambient temperature for 18 h. The mixture is filtered through Celite, and the filtrate is concentrated to give the title compound as an oil, which is used directly in the next step.

Workup

  1. filtrationThe mixture is filtered through Celite
  2. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-fbecffe5ad344acd9a6bc59c194294b5
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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