5-(5-Aza-spiro[2.4]hept-5-yl)-4-chloro-2-nitro-phenylamine → 4-(5-Aza-spiro[2.4]hept-5-yl)-5-chloro-benzene-1,2-diamine

HRID 1258642Notes

Reaction equation

HRID 1258642 reaction equation
[CH2:1]1[C:3]2([CH2:7][CH2:6][N:5]([C:8]3[C:9]([Cl:18])=[CH:10][C:11]([N+:15]([O-])=O)=[C:12]([NH2:14])[CH:13]=3)[CH2:4]2)[CH2:2]1>[Ni].CCOC(C)=O>[CH2:1]1[C:3]2([CH2:7][CH2:6][N:5]([C:8]3[CH:13]=[C:12]([NH2:14])[C:11]([NH2:15])=[CH:10][C:9]=3[Cl:18])[CH2:4]2)[CH2:2]1

Participants

4

Reactant 1

HCID 679585435-(5-Aza-spiro[2.4]hept-5-yl)-4-chloro-2-nitro-phenylamine

Product 1

HCID 679578314-(5-Aza-spiro[2.4]hept-5-yl)-5-chloro-benzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-(5-aza-spiro[2.4]hept-5-yl)-4-chloro-2-nitro-phenylamine (550 mg, 2.1 mmol), EtOAc (20 mL) and Ra—Ni (150 mg) was stirred for 21 h at RT under a hydrogen atmosphere (3 bar). After addition of further catalyst the hydrogenation was continued at rt for 7 h. The catalyst was removed by filtration. The filtrate was acidified with 1.25 M HCl in EtOH (6 mL) and concentrated to give the sub-title compound.

Workup

  1. additionAfter addition of further catalyst the hydrogenation
  2. waitwas continued at rt for 7 h
  3. customThe catalyst was removed by filtration
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-79b9a4646e0f4a6d85d321151601cdf7
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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