Ethyl 4-chloro-1-methyl-3-[(2-nitrophenyl)amino]-1H-pyrrole-2-carboxylate → HCID 13578541, compound

HRID 465055Notes

Reaction equation

HRID 465055 reaction equation
[Cl:1][C:2]1[C:3]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N+:20]([O-])=O)=[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:5]([CH3:7])[CH:6]=1>O1CCCC1.[Ni]>[NH2:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[NH:13][C:3]1[C:2]([Cl:1])=[CH:6][N:5]([CH3:7])[C:4]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

4

Reactant 1

HCID 13578540Ethyl 4-chloro-1-methyl-3-[(2-nitrophenyl)amino]-1H-pyrrole-2-carboxylate

Product 1

HCID 13578541HCID 13578541, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 4-chloro-1-methyl-3-[(2-nitrophenyl) amino]-1H-pyrrole-2-carboxylate (35.6 g, 0.11 mol) in tetrahydrofuran (700 ml) is hydrogenated for 10 hours under a hydrogen pressure of 10 bar and at a temperature of 40° C. after the addition of Raney nickel (10 g). After a further Raney nickel (10 g) had been added, hydrogenation is continued for a further 13 hours under the same conditions, after which no further starting material is detected in the mixture by thin layer chromatography. The catalyst is filtered off, the filtrate is concentrated in vacuo and the syrupy residue is recrystallized once from tert.butyl methyl ether and once from methanol. The colorless crystals (27.5 g) melted at 104° to 105° C.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated in vacuo
  3. customthe syrupy residue is recrystallized once from tert.butyl methyl ether and once from methanol

Sources & evidence

ORD record
ord-338194ce44e14ff28f7a9fa100c7943e
Source dataset
uspto-grants-1985_10
Patent number
US04550107

Reaction notes

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