Methyl 4-aminobenzoate → HCID 178498128, compound

HRID 1801271Notes

Reaction equation

HRID 1801271 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[NH2:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=1>>[Cl:1][C:2]1[CH:9]=[CH:8][C:5](/[CH:6]=[N:13]/[C:14]2[CH:15]=[CH:16][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:22][CH:23]=2)=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

Participants

3

Reactant 2

HCID 12082Methyl 4-aminobenzoateHCID 855054-Chloro-3-nitrobenzaldehyde

Product 1

HCID 178498128HCID 178498128, compoundYield 98.4%

Procedure

To a solution of 4-chloro-3-nitrobenzaldehyde (5.0 g, 27 mmol) in 42 mL of ethonal was added methyl 4-aminobenzoate (4.07 g, 27 mmol), and the reaction mixture was stirred over weekend. The yellow precipitates were filtered, and 8.47 g of (E)-methyl 4-(4-chloro-3-nitrobenzylidenamino)benzoate a yellow solid was obtained. (Yield=98%). (E)-methyl 4-(4-chloro-3-nitrobenzylideneamino)benzoate (8.47 g, 26.6 mmol) and yttrium(III) trifluoromethanesulfonate (800 mg, 1.33 mmol) was dissolved in dry tetrahydrofuran (100 mL), and then cooled below 0° C. Isobutyl aldehyde (2.30 g, 31.9 mmol) was added below 0° C. The reaction mixture was stirred at room temperature overnight. Thin layer chromatography showed most of starting material was consumed. 50 mL of ethyl acetate and 50 mL of water were added to the mixture, and the separated organic layer was washed with brine again. The organic layer was dried over sodium sulfate and purified on silica gel to afford 4.9 g of methyl 2-(4-chloro-3-nitrophenyl)-4-hydroxy-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate. (Yield=47%). MS (ESI+APCI) M+1=373.

Workup

  1. customThe yellow precipitates
  2. filtrationwere filtered

Sources & evidence

ORD record
ord-a4e95608e46d4bf5abf3829405ba8212
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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