Potassium Carbonate → Methyl 2-[N-(tert-Butoxycarbonyl)-N-[(2'-cyanobiphenyl-4-yl)methyl]amino]-3-nitrobenzoate

HRID 567396Notes

Reaction equation

HRID 567396 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[C:10]#[N:11])=[CH:4][CH:3]=1.[C:16]([O:20][C:21]([NH:23][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])=[O:22])([CH3:19])([CH3:18])[CH3:17].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:16]([O:20][C:21]([N:23]([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])[CH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[C:10]#[N:11])=[CH:6][CH:7]=1)=[O:22])([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1455122-Cyano-4'-methylbiphenylHCID 9965968Methyl 2-((tert-butoxycarbonyl)amino)-3-nitrobenzoate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
82 °C

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. additionwas added
  2. customthe reaction
  3. temperatureThe solution was cooled to room temperature
  4. customprecipitated crystals
  5. filtrationwere filtered off
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-9697696736794bbbbeed3970c5a9a5f8
Source dataset
uspto-grants-2001_01
Patent number
US06177587B1

Reaction notes

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