Water → 2-Chloro-1-methyl-1H-indole-3-carbaldehyde

HRID 751331

반응식

HRID 751331 반응식
[Cl:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH:11]=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.[H-].[Na+].[CH3:15]I.O>CN(C=O)C>[Cl:1][C:2]1[N:3]([CH3:15])[C:4]2[C:9]([C:10]=1[CH:11]=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2

참가 물질

6

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 3147912-chloro-1H-indole-3-carbaldehyde

생성물 1

HCID 3147922-Chloro-1-methyl-1H-indole-3-carbaldehyde수율 108.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 2-chloro-1H-indole-3-carboxaldehyde (1.0 g, 5.5 mmol) in DMF (30 mL) is treated portionwise over 10 min with 60% sodium hydride (440 mg, 11 mmol). After stirring for 30 min, methyl iodide (685 μL, 11 mmol) is slowly added and the resulting mixture is stirred 3 hr at room temperature. Water (5 mL) is cautiously added and the solvents are removed. The residue is dissolved in ethyl acetate and washed with water, with brine, dried, filtered and concentrated to give 2-chloro-1-methyl-1H-indole-3-carboxaldehyde (1.16 g, 105%), mp 94.5-95.5° C., as a white solid. MS 194 (M+H).

후처리

  1. stirringthe resulting mixture is stirred 3 hr at room temperature
  2. customthe solvents are removed
  3. dissolutionThe residue is dissolved in ethyl acetate
  4. washwashed with water, with brine
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-db7c0c23a38e4024ba0f91b3d240dd7d
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07405300B2

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