Ammonium Chloride → 1-[3-Amino-4-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-ethanone

HRID 1711255Notes

Reaction equation

HRID 1711255 reaction equation
[CH3:1][C:2]1([CH3:20])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:16])[CH3:15])=[CH:10][C:9]=2[N+:17]([O-])=O)=[CH:4][CH2:3]1.[NH4+].[Cl-]>[Fe].CCOC(C)=O.CCCCCC>[NH2:17][C:9]1[CH:10]=[C:11]([C:14](=[O:16])[CH3:15])[CH:12]=[CH:13][C:8]=1[C:5]1[CH2:6][CH2:7][C:2]([CH3:1])([CH3:20])[CH2:3][CH:4]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 587548131-[4-(4,4-Dimethyl-cyclohex-1-enyl)-3-nitro-phenyl]-ethanone

Product 1

HCID 587548621-[3-Amino-4-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-ethanoneYield 77%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 21226206Ethyl acetate hexaneSolvent

Procedure

The title compound was prepared by the procedure of Example 19, using 1-[4-(4,4-dimethyl-cyclohex-1-enyl)-3-nitro-phenyl]-ethanone (as prepared in the previous step, 382 mg, 1.40 mmol), iron powder (391 mg, 7.00 mmol), and NH4Cl (749 mg, 14.0 mmol). Silica gel chromatography (5-20% EtOAc/hexane) afforded the title compound (263 mg, 77%) as a faint yellow solid. Mass spectrum (ESI, m/z): Calcd. for C16H21NO, 244.2 (M+H), found 244.2.

Workup

  1. customThe title compound was prepared by the procedure of Example 19

Sources & evidence

ORD record
ord-7ac4cf7009584ccda2841b0aa73e1691
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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