Methyl 4-aminobenzoate → HCID 178498131, compound

HRID 2045570Notes

Reaction equation

HRID 2045570 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-1b0f476375324592a90545d471f3fac9
Source dataset
uspto-grants-2013_11
Patent number
US08586747B2

Reaction notes

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