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

HRID 567397Notes

Reaction equation

HRID 567397 reaction equation
C(OC([N:8]([C:24]1[C:33]([N+:34]([O-:36])=[O:35])=[CH:32][CH:31]=[CH:30][C:25]=1[C:26]([O:28][CH3:29])=[O:27])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]#[N:23])=[CH:12][CH:11]=1)=O)(C)(C)C.Cl>CO>[C:22]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:13]1[CH:14]=[CH:15][C:10]([CH2:9][NH:8][C:24]2[C:33]([N+:34]([O-:36])=[O:35])=[CH:32][CH:31]=[CH:30][C:25]=2[C:26]([O:28][CH3:29])=[O:27])=[CH:11][CH:12]=1)#[N:23]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10874596Methyl 2-[N-(tert-Butoxycarbonyl)-N-[(2'-cyanobiphenyl-4-yl)methyl]amino]-3-nitrobenzoate

Product 1

HCID 15654651Methyl 2-{[(2'-cyano[1,1'-biphenyl]-4-yl)methyl]amino}-3-nitrobenzoateYield 76.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the acetonitrile solution where BMB is mixing with 2-(4-methylphenyl)benzonitrile [MPB] which was not brominated and 2-(4,4-dibromomethylphenyl)benzonitrile which is a compound similar to BMB, was added a mixture of methyl 2-tert-butoxycarbonylamino-3-nitrobenzoate [BAN] 30.1 g, potassium carbonate 40.8 g and acetonitrile 160 ml and the solution was stirred at about 82° C. for about 5 hours to proceed the reaction. The solution was cooled to room temperature and precipitated crystals were filtered off. The filtrate was concentrated to give methyl 2-[N-t-butoxycarbonyl-N-[(2′-cyano-biphenyl-4-yl)methyl]amino]-3-nitrobenzoate [BBN]. The concentrate was dissolved in methanol 190 g. To the methanol solution was dropped concentrated hydrochloric acid 106 g and the solution was heated to refluxing temperature for 2 hours and thereafter stirred under reflux for 2 hours to proceed the reaction. The reaction solution was cooled and the precipitated crystals were filtered and dried to give methyl 2-[N-(2′-cyanobiphenyl-4-yl)methylamino]-3-nitrobenzoate [MBN] 35.1 g (yield based on 2-(4-methylphenyl)benzonitrile [MPB]: 76.1%).

Workup

  1. temperaturethe solution was heated
  2. temperatureto refluxing temperature for 2 hours
  3. temperatureunder reflux for 2 hours
  4. customthe reaction
  5. temperatureThe reaction solution was cooled
  6. filtrationthe precipitated crystals were filtered
  7. customdried

Sources & evidence

ORD record
ord-ddea105c907c4c10a23ed3561382485d
Source dataset
uspto-grants-2001_01
Patent number
US06177587B1

Reaction notes

Loading…