4-Chloro-benzoic Acid 1-(4-Methoxyphenyl)hydrazide Hydrochloride → 3-(1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl)-2-methylpropanoic acid

HRID 527447Notes

Reaction equation

[CH3:1][CH:2]([CH2:6][C:7](=O)[CH2:8][CH3:9])[C:3]([OH:5])=[O:4].Cl.[Cl:12][C:13]1[CH:30]=[CH:29][C:16]([C:17]([N:19]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)N)=[O:18])=[CH:15][CH:14]=1>C(O)(=O)C>[Cl:12][C:13]1[CH:30]=[CH:29][C:16]([C:17]([N:19]2[C:21]3[C:22](=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=3)[C:8]([CH3:9])=[C:7]2[CH2:6][CH:2]([CH3:1])[C:3]([OH:5])=[O:4])=[O:18])=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 80 °C

Procedure

2-methyl-4-oxohexanoic acid (27.6 mg, 0.19 mmol) was added to a stirred solution of 4-chloro-N-(4-methoxyphenyl)benzohydrazide hydrochloride (50 mg, 0.16 mmol) in acetic acid (0.5 mL), the mixture was heated at 80° C. under nitrogen for 3 h, then it was allowed to cool to ambient temperature and stirred overnight. Ice-water (2 mL) was poured into the cold reaction mixture and the formed precipitate was collected by filtration, carefully washed with water and dried in vacuo to yield the title compound (27 mg, 44%) as an off-white solid. C21H20ClNO4, Mr=385.84; 1H NMR (400 MHz, DMSO-d6) d: 1.01 (d, J=6.8 Hz, 3H), 2.19 (s, 3H), 2.54 (sex, J=7.2 Hz, 1H), 2.91-3.19 (m, 2H), 3.76 (s, 3H), 6.46 (d, J=9.2 Hz, 1H), 6.64 (dd, J=2.4/9.0 Hz, 1H), 7.02 (d, J=2.4 Hz, 1H); LCMS (ESI) tR: 2.78 min (>99%, ELSD), m/z: 386.1 [M+1]+.

Workup

temperatureto cool to ambient temperature
filtrationthe formed precipitate was collected by filtration
washcarefully washed with water
customdried in vacuo

Sources & evidence

ORD record: ord-adfe4f51a13d4a58b4fd4e3818a5a46e
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346803B2

Reaction notes

Loading…