tert-Butyl 4-(4-methylpiperazin-1-yl)-2-nitrobenzoate → 2-Amino-4-(4-methylpiperazin-1-yl) benzoic acid tertbutyl ester

HRID 1640974Notes

Reaction equation

[C:1]([O:5][C:6](=[O:23])[C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)=[CH:9][C:8]=1[N+:20]([O-])=O)([CH3:4])([CH3:3])[CH3:2]>[Pd].C(O)C>[C:1]([O:5][C:6](=[O:23])[C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)=[CH:9][C:8]=1[NH2:20])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 4-(4-methyl-piperazin-1-yl)-2-nitro-benzoic acid tert-butyl ester (13.3 g, 41.5 mmol) cyclohexene (45 mL), ethanol (300 mL) and 10% Pd/C (0.4 g) was stirred at 80° C. for 7 hours. Additional 10% Pd/C was added (0.9 g) and the mixture stirred at 80° C. for additional 4 hours. The reaction mixture was filtered over a celite pad washing thoroughly with ethanol and the filtrate was evaporated to dryness affording the title compound as a pale yellow solid (11.5 g, 95% yield).

Workup

stirringthe mixture stirred at 80° C. for additional 4 hours
filtrationThe reaction mixture was filtered over a celite pad
washwashing thoroughly with ethanol
customthe filtrate was evaporated to dryness

Sources & evidence

ORD record: ord-fac6370beb3448e1a37de26098d8966d
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08114865B2

Reaction notes

Loading…