Ammonium Acetate → 3-[(3-fluoro-6-methylphenanthridin-5(6H)-yl)carbonyl]phenol

HRID 731985Notes

Reaction equation

HRID 731985 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:15]([NH2:17])[CH3:16].FC1C=C(F)C=CC=1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[C:32](=[O:34])C.C([O-])(=[O:37])C.[NH4+].C([BH3-])#N.[Na+]>CO>[F:8][C:6]1[CH:7]=[CH:2][C:3]2[C:9]3[C:10]([CH:15]([CH3:16])[N:17]([C:32]([C:27]4[CH:28]=[C:29]([OH:37])[CH:30]=[CH:31][CH:26]=4)=[O:34])[C:4]=2[CH:5]=1)=[CH:11][CH:12]=[CH:13][CH:14]=3

Participants

6

Reactant 4

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 224822721-(2',4'-Difluoro-1,1'-biphenyl-2-yl)ethanoneHCID 224823761-[2-(2,4-Difluorophenyl)phenyl]ethan-1-amine

Product 1

HCID 115009123-[(3-fluoro-6-methylphenanthridin-5(6H)-yl)carbonyl]phenol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(-2′,4′-difluoro-biphenyl-2-yl)-ethylamine—The title compound was prepared from 1-(2′,4′-difluoro-1,1′-biphenyl-2-yl)ethanone (3.67 g, 15.8 mmol), anhydrous methanol (200 mL), ammonium acetate (12.2 g, 158 mmol), and sodium cyanoborohydride (1.99 g, 31.6 mmol) according to the procedure and in the same manner as described in Example 24, step b resulting in the isolation of a clear oil that was used without further purification. MS [(ES+), m/z]: 217 [M-16]+, benzylic cation as a result of the loss of NH2.

Workup

  1. customresulting in the isolation of a clear oil that
  2. customwas used without further purification
  3. customMS [(ES+), m/z]: 217 [M-16]+, benzylic cation as a result of the loss of NH2

Sources & evidence

ORD record
ord-1b36fa801b1d4d6c9ac0302aa85ce949
Source dataset
uspto-grants-2009_09
Patent number
US07585871B2

Reaction notes

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