Ammonium Hydroxide → 2-Amino-4-methylbenzonitrile

HRID 471589

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HRID 471589 반응식
Br[C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C([Cu])#[N:12].[NH4+].[OH-]>CN1C(=O)CCC1>[NH2:12][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

참가 물질

5

반응물 3

HCID 14923Ammonium HydroxideHCID 8208022-Bromo-4-methylbenzonitrileHCID 178418546HCID 178418546, 화합물

생성물 1

HCID 28012762-Amino-4-methylbenzonitrile수율 88%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

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온도
0 °C

실험 절차

A solution of 2-bromo-4-methylbenzonitrile (2.0 g, 10.7 mmol) and CuCN (1.92 g, 21.4 mmol) in NMP (10 mL) was reacted in a microwave for 20 min at 200° C. Upon completion the reaction was cooled to 0° C., and 15% aqueous NH4OH (215 mL) was slowly added. The mixture was stirred at rt for 30 min, then extracted with CH2Cl2. The organic layer was washed with H2O, brine, dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (3:1 Hexane:EtOAc) to provide 2-amino-4-methylbenzonitrile (1.24 g, 88%). 1H NMR (400 MHz, CDCl3) δ 1.45 (s, 3H), 5.70 (m, 1H), 5.84 (m, 1H), 6.41 (d, J=8.0 Hz, 1H).

후처리

  1. extractionextracted with CH2Cl2
  2. washThe organic layer was washed with H2O, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (3:1 Hexane:EtOAc)

출처 및 근거

ORD 기록
ord-2e355610288649758aedb4884ecb2884
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633186B2

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