Ammonia → 2-[4-(Aminomethyl)-3-methylphenyl]-2-methylpropanenitrile

HRID 603142ノート

反応式

HRID 603142 の反応式
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH3:13])([CH3:12])[C:10]#[N:11])=[CH:5][C:4]=1[CH3:14])=O.[BH4-].[Na+].[NH3:17]>CO.CC(O[Ti](OC(C)C)(OC(C)C)OC(C)C)C>[NH2:17][CH2:1][C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH3:13])([CH3:12])[C:10]#[N:11])=[CH:5][C:4]=1[CH3:14]

参加物

6

反応物 3

HCID 222AmmoniaHCID 4311764Sodium borohydrideHCID 582984532-(4-Formyl-3-methylphenyl)-2-methylpropanenitrile

生成物 1

HCID 582984482-[4-(Aminomethyl)-3-methylphenyl]-2-methylpropanenitrile収率 87%

試薬・触媒・溶媒 2

HCID 178460666HCID 178460666、化合物触媒HCID 887Methanol溶媒

実験手順

2-(4-formyl-3-methylphenyl)-2-methylpropanenitrile 1.89 g, 10.2 mmol) is dissolved in 50 ml of 7M NH3 in MeOH. Ti(OiPr)4 (6 mmol, 20 mmol) is added and the mixture stirred for 3 hours at room temperature. NaBH4 (0.6 g, 15 mmol) is added and the reaction left at room temperature overnight. The mixture is quenched by the addition of 25 ml of NH4OH 2 M. The resulting precipitate is filtered off and washed with EtOAc. Phases are separated, the organic phase is dried over magnesium sulfate, filtered and evaporated to dryness, giving 2-[4-(aminomethyl)-3-methylphenyl]-2-methylpropanenitrile (1.325 g, 7.09 mmol, 87%). The crude product is used without further purification. 1H NMR (400 MHz, DMSO-D6) δ 1.64 (s, 6H, first rotamer) 1.65 (s, 6H, second rotamer) 2.28 (s, 3H, first rotamer) 2.29 (s, 3H, second rotamer) 3.32 (broad s, 2H) 3.67 (s, 2H, first rotamer) 3.68 (s, 2H, second rotamer) 7.24-7.27 (m, 1H) 7.28 (s, 1H) 7.36-7.40 (m, 1H).

後処理

  1. waitthe reaction left at room temperature overnight
  2. customThe mixture is quenched by the addition of 25 ml of NH4OH 2 M
  3. filtrationThe resulting precipitate is filtered off
  4. washwashed with EtOAc
  5. customPhases are separated
  6. dry with materialthe organic phase is dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness

出典と根拠

ORDレコード
ord-d137a0f6c75b4178ba2e7bbd98549db7
出典データセット
uspto-grants-2011_03
特許番号
US07906654B2

反応ノート

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