Benzene → HCID 86742220, compound

HRID 579996Notes

Reaction equation

HRID 579996 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH:11]=O)[C:5]([OH:7])=[O:6].[CH2:13]([NH2:17])[CH2:14][CH2:15][CH3:16].C1C=CC=CC=1>O>[Cl:1][CH:2]1[C:10](=[C:11]=[N:17][CH2:13][CH2:14][CH2:15][CH3:16])[CH:9]=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[CH:3]1

Participants

5

Reactant 3

HCID 241BenzeneHCID 8007ButylamineHCID 12290536HCID 12290536, compound

Product 1

HCID 86742220HCID 86742220, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Chloro-4-formylbenzoic acid (5 g, 0.027 mole), butylamine (2 g, 0.027 mole) and benzene (75 ml) were refluxed for 2 hours using a flask fitted with a Dean-Stark water separator. The solvent was removed by distillation in vacuo to give 3-chloro-4-(butyliminomethylene) benzoic acid to which was added nitropropane (8.9 g, 0.1 mole) and acetic acid (21 ml). The mixture was refluxed for 10 minutes then cooled in ice. The mixture was treated with water and the solid that separated removed by filtration, washed with water, dried and recrystallized from a mixture of acetic acid and water (2:1) to give 4.7 g of the desired product, m.p. 179°-180° C.

Workup

  1. customThe solvent was removed by distillation in vacuo

Sources & evidence

ORD record
ord-e1d72179636743fda74c8162d4e71107
Source dataset
uspto-grants-1988_06
Patent number
US04751244

Reaction notes

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