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

HRID 1057654

反応式

HRID 1057654 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ba9fc0c934af441c8889951a80f68c8e
出典データセット
uspto-grants-2003_02
特許番号
US06514968B1

関連ノート

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