Ethyl 1-(4-nitrophenyl)cyclopropanecarboxylate → Ethyl 1-(4-aminophenyl)cyclopropanecarboxylate

HRID 1400130Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O>O1CCCC1.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:12][CH2:11]2)=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 23 °C

Procedure

11.3 g of ethyl 1-(4-nitrophenyl)cyclopropanecarboxylate are dissolved in 110 ml of tetrahydrofuran, 1 g of 5% Pd/C (52.3% of water) is added, and the mixture is stirred at 23° C. under a hydrogen atmosphere for 1 h. After aeration, the solid material is filtered off, and the filtrate is evaporated to dryness in vacuo. Yield: 9.8 g (100%) of ethyl 1-(4-aminophenyl)cyclopropanecarboxylate; LC-MS retention time: 1.18 min (“nonpolar” gradient).

Workup

filtrationAfter aeration, the solid material is filtered off
customthe filtrate is evaporated to dryness in vacuo

Sources & evidence

ORD record: ord-76929378e6674268ad39801a23574216
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906930B2

Reaction notes

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