HCID 57917356, compound → HCID 57917314, compound

HRID 69142Notes

Reaction equation

HRID 69142 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[C:6]([NH:13][CH2:14][CH2:15][N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:5]=1>CO.C1COCC1.[Ni]>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([NH:13][CH2:14][CH2:15][N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:5]=1

Participants

4

Reactant 1

HCID 57917356HCID 57917356, compound

Product 1

HCID 57917314HCID 57917314, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

4-Nitro-3-(2-pyrrolidin-1-yl-ethylamino)-benzoic acid methyl ester (xiii) (1.30 g, 4.42 mmol) was shaken in MeOH/THF 1:1 (40 mL) in presence of Raney nickel under 1.1 bar H2 at rt for 40 min. The catalyst was filtered off and washed with MeOH. The filtrate was evaporated to give the title compound as an oil (tR 2.05 min (conditions 8), MH+=264).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with MeOH
  3. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-f5692c16fcfe4d2895f31b62da87a115
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

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