Pyrrolidine → HCID 13912882, compound

HRID 1789076Notes

Reaction equation

HRID 1789076 reaction equation
[NH2:1][C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[NH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1>CN(C)C=O>[NH2:1][C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([N:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1)=[O:9]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 13912874HCID 13912874, compound

Product 1

HCID 13912882HCID 13912882, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4.24 g of 5-amino-2-methoxy-4-nitrobenzoic acid in 30 ml of N,N-dimethylformamide was added 3.24 g of N,N'-carbonyldiimidazole at room temperature. After 30 minutes, 5 ml of pyrrolidine was added, and the mixture was stirred for 2 hours. The solvent was evaporated under reduced pressure, and the residue was recrystallized from ethyl acetate to give the title compound, m.p. 159°-162° C., yield of 4.16 g.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-bcfdfddfae3a43ad965c1d4f29ef6011
Source dataset
uspto-grants-1987_08
Patent number
US04686292

Reaction notes

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