Hydrochloric Acid → Methyl 2-{[(2'-cyano[1,1'-biphenyl]-4-yl)methyl]amino}-3-nitrobenzoate

HRID 567400Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:36])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1[N:13](C(OC(C)(C)C)=O)[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]#[N:28])=[CH:17][CH:16]=1.Cl>CO>[C:27]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:18]1[CH:19]=[CH:20][C:15]([CH2:14][NH:13][C:5]2[C:6]([N+:10]([O-:12])=[O:11])=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([O:2][CH3:1])=[O:36])=[CH:16][CH:17]=1)#[N:28]

Participants

Conditions

Temperature: 68 °C

Procedure

The concentrate obtained in Working Example 2(2) (methyl2-[N-t-butoxycarbonyl-N-[(2′-cyanobiphenyl-4-yl)methyl]amino]-3-nitro-benzoate [BBN]) and methanol (3200 L) were mixed, and 35% concentrated hydrochloric acid (1050 L) was added to the mixture at 30° C. or less for about 4 hours. The mixture was heated to reflux temperature (67-69° C.) at a speed of 10° C. or less/hour, and stirred for about 1.5 hours under reflux. The reaction solution was cooled, to which was added methanol (800 L), and the solution was stirred at 3-10° C. for about 1 hour. The precipitated crystals were separated, washed with methanol and dried to give methyl 2-[[(2′-cyano-biphenyl-4-yl)methyl]amino]-3-nitro-benzoate [MBN] (407 kg; yield based on MPB: 75%).

Workup

additionwere mixed
temperatureThe mixture was heated
temperatureunder reflux
temperatureThe reaction solution was cooled, to which
stirringthe solution was stirred at 3-10° C. for about 1 hour
customThe precipitated crystals were separated
washwashed with methanol
customdried

Sources & evidence

ORD record: ord-ba10546a87d64a158a53099b373b5c22
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06177587B1

Reaction notes

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