Benzyl Bromide → 9-Benzyl-6-methoxy-1,2,3,9-tetrahydro-4H-carbazol-4-one

HRID 1057654

반응식

HRID 1057654 반응식
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]1[CH2:12][CH2:11][CH2:10][C:9](=[O:18])[C:8]2=1.[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C>[CH2:19]([N:14]1[C:13]2[CH2:12][CH2:11][CH2:10][C:9](=[O:18])[C:8]=2[C:7]2[C:15]1=[CH:16][CH:17]=[C:5]([O:4][CH3:3])[CH:6]=2)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 152128016-Methoxy-1,2,3,9-tetrahydro-4H-carbazol-4-one

생성물 1

HCID 111095159-Benzyl-6-methoxy-1,2,3,9-tetrahydro-4H-carbazol-4-one수율 81.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

To a slurry of 60% sodium hydride (0.76 g, 19.6 mmol) in DMF (20 mL) is added 6-methoxy-1,2,3,9-tetrahydro-4H-carbazol-4-one (3.84 g, 17.8 mmol) over a period of 5 minutes and benzyl bromide (2.4 mL, 19.6 mmol). The mixture is heated to 50° C. for 1 hour then room temperature overnight. The mixture is partitioned between water and CH2Cl2. The layers are separated and the organic layer washed with water (200 mL) and concentrated. The residue is triturated in hexanes and filtered to give 4.45 g (80%) of the title compound; mp 174-175° C., IR (drift) 2939, 1633, 1484, 1467, 1448, 1349, 1276, 1242, 1159, 1130, 1099, 854, 791, 762, 710 cm−1. 1H NMR (DMSO-d6) δ2.1, 2., 2.93, 3.75, 5.44, 6.77, 7.09, 7.28, 7.39, 7.51; Anal. Calcd for C20H19NO2: C, 78.66; H, 6.27; N, 4.59. Found: C, 78.45; H, 6.31; N, 4.58.

후처리

  1. customroom temperature overnight
  2. customThe mixture is partitioned between water and CH2Cl2
  3. customThe layers are separated
  4. washthe organic layer washed with water (200 mL)
  5. concentrationconcentrated
  6. customThe residue is triturated in hexanes
  7. filtrationfiltered

출처 및 근거

ORD 기록
ord-ba9fc0c934af441c8889951a80f68c8e
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06514968B1

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