Ammonia methanol → 3-(Aminomethyl)-5-(trifluoromethyl)benzonitrile

HRID 604219Notes

Reaction equation

HRID 604219 reaction equation
Br[C:2]1[C:3](C)=[C:4]([CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)[C:5]#[N:6].[NH3:15].[CH3:16]O>>[NH2:6][CH2:5][C:4]1[CH:3]=[C:2]([CH:9]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:7]=1)[C:16]#[N:15]

Participants

3

Reactant 2

HCID 21705897Ammonia methanolHCID 666029993-Bromo-methyl-5-trifluoromethyl-benzonitrile

Product 1

HCID 451158403-(Aminomethyl)-5-(trifluoromethyl)benzonitrile

Conditions

Temperature
55 °C

Procedure

3-Bromomethyl-5-trifluoromethyl-benzonitrile (which is prepared in Reference Example 12) (15.9 g) is dissolved in 7M-ammonia/methanol (550 ml), and the mixture is stirred at 50-60° C. for 30 minutes. The reaction solution is concentrated under reduced pressure. To the resulting residue are added a saturated aqueous sodium bicarbonate solution and chloroform, and the mixture is separated, and the organic layer is dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (chloroform:methanol=1:0→19:1 chloroform:methanol: ammonium hydroxide solution=19:1:0.1) to give 3-aminomethyl-5-trifluoromethyl-benzonitrile (10.4 g). MS (m/z): 201 [M+H]+

Workup

  1. concentrationThe reaction solution is concentrated under reduced pressure
  2. additionTo the resulting residue are added a saturated aqueous sodium bicarbonate solution and chloroform
  3. customthe mixture is separated
  4. dry with materialthe organic layer is dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue is purified by silica gel column chromatography (chloroform:methanol=1:0→19:1 chloroform:methanol: ammonium hydroxide solution=19:1:0.1)

Sources & evidence

ORD record
ord-622e3cb1c7e24997827c298b115b91ff
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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