3-Nitrobenzaldehyde → HCID 70060471, compound

HRID 1762473Notes

Reaction equation

HRID 1762473 reaction equation
[C:1]([O:7][CH2:8][CH2:9][CH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][NH:11]1)(=[O:6])[CH2:2][C:3]([CH3:5])=O.[N+:19]([C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH:25]=O)([O-:21])=[O:20].[NH2:30]/[C:31](/[CH3:37])=[CH:32]\[C:33]([O:35][CH3:36])=[O:34]>CC(O)C>[CH3:5][C:3]1[NH:30][C:31]([CH3:37])=[C:32]([C:33]([O:35][CH3:36])=[O:34])[CH:25]([C:24]2[CH:27]=[CH:28][CH:29]=[C:22]([N+:19]([O-:21])=[O:20])[CH:23]=2)[C:2]=1[C:1]([O:7][CH2:8][CH2:9][CH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][NH:11]1)=[O:6]

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 57241265HCID 57241265, compound

Product 1

HCID 70060471HCID 70060471, compoundYield 46.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 1.54 g (6.2 m mol) of 2-isoindolinylethyl acetoacetate, 0.942 g (6.2 m mol) of 3-nitrobenzaldehyde and 0.717 g (6.2 m mol) of methyl 3-aminocrotonate in 37 ml of 2-propanol was heated at 80° C. under nitrogen for 48 hours. The crude mixture was concentrated in vacuo and subjected to flash chromatography (silica gel, 1:1 petroleum ether/ethyl acetate) to give 1.38 g (46%) of a brown solid, m.p. 63°-69° C. NMR (CDCl3) δ 2.29 (6H, s), 2.8 (2H, t), 3.5 (2H, s), 3.8 (4H, s), 4.12 (2H, t), 5.0 (1H, s), 6.2 (1H, bs), 7.33 (8H, m).

Workup

  1. concentrationThe crude mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-8739ab82094f477fb14d2269c0349f47
Source dataset
uspto-grants-1989_05
Patent number
US04833150

Reaction notes

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