Methanol → HCID 178508149, compound

HRID 2218971Notes

Reaction equation

HRID 2218971 reaction equation
[C:1]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][C:4]([NH2:7])=[C:3]([NH2:8])[CH:2]=1.CO.O.[N:18]#[C:19]Br>C1COCC1>[C:9]1([C:1]2[CH:6]=[CH:5][C:4]3[NH:7][C:19]([NH2:18])=[N:8][C:3]=3[CH:2]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 10476Cyanogen BromideHCID 6452000(1,1'-Biphenyl)-3,4-diamine

Product 1

HCID 178508149HCID 178508149, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of biphenyl-3,4-diamine (0.99 mmol) in THF:MeOH:water (5 mL:10 mL:10 mL) was added cyanogen bromide (5M solution in acetonitrile, 1.06 mmol). The resulting mixture was stirred at room temperature overnight. The reaction was partitioned between EtOAc and aqueous sodium hydroxide and the aqueous layer re-extracted with EtOAc. The combined EtOAc extracts were washed with water, brine, dried over MgSO2, then concentrated in vacuo to afford 7 (147 mg, 71%) as an off-white solid.

Workup

  1. customThe reaction was partitioned between EtOAc and aqueous sodium hydroxide
  2. extractionthe aqueous layer re-extracted with EtOAc
  3. washThe combined EtOAc extracts were washed with water, brine
  4. dry with materialdried over MgSO2
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e4d567a74cd846cb8054652dbd491677
Source dataset
uspto-grants-2008_08
Patent number
US07414046B2

Reaction notes

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