Methyl 4-aminobenzoate → HCID 178498131, compound

HRID 1801291Notes

Reaction equation

HRID 1801291 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][C:14]=1[N+:21]([O-:23])=[O:22]>C(O)C>[F:12][C:13]1[CH:20]=[CH:19][C:16](/[CH:17]=[N:1]/[C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=2)=[CH:15][C:14]=1[N+:21]([O-:23])=[O:22]

Participants

4

Reactant 2

HCID 12082Methyl 4-aminobenzoateHCID 5981294-Fluoro-3-nitrobenzaldehyde

Product 1

HCID 178498131HCID 178498131, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of methyl 4-aminobenzoate (4.57 g, 30.2 mmol) and 4-fluoro-3-nitrobenzaldehyde (5.00 g, 29.6 mmol) in ethanol (30 mL) was stirred at room temperature for 16 hours (precipitates formed within 30 min). The solid product was collected by filtration and the trace amount of solvent was removed under vacuum. 8.32 g (83%) of (E)-methyl 4-(4-fluoro-3-nitrobenzylideneamino)benzoate was obtained as a yellow solid.

Workup

  1. custom(precipitates formed within 30 min)
  2. filtrationThe solid product was collected by filtration
  3. customthe trace amount of solvent was removed under vacuum

Sources & evidence

ORD record
ord-d6181a5b5a3e4fc1b474f9cf7b5373e6
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

Loading…