Potassium Carbonate → (6-chloro-2-(4-chlorobenzoyl)-1H-indol-3-yl)acetic acid

HRID 396573ノート

反応式

HRID 396573 の反応式
C([O:3][C:4](=[O:25])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[NH:14]S(C1C=CC(C)=CC=1)(=O)=O)C.C(=O)([O-])[O-].[K+].[K+].Br[CH2:33][C:34]([C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=1)=[O:35].[OH-].[Na+]>CN(C)C(=O)C>[Cl:13][C:10]1[CH:9]=[C:8]2[C:7]([C:6]([CH2:5][C:4]([OH:3])=[O:25])=[C:33]([C:34](=[O:35])[C:36]3[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=3)[NH:14]2)=[CH:12][CH:11]=1

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 68303p-Chlorophenacyl bromideHCID 53985536HCID 53985536、化合物

生成物 1

HCID 9798374(6-chloro-2-(4-chlorobenzoyl)-1H-indol-3-yl)acetic acid収率 82%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

実験手順

To a solution of 3-[4-chloro-2-(toluene-4-sulfonylamino)-phenyl]-acrylic acid ethyl ester (13.0g, 34.2 mmol) in N,N-dimethylacetamide (120 ml) was added potassium carbonate (9.45 g, 68.4 mmol) and 2-bromo-4′-chloroacetophenone (8.78 g, 37.6 mmol) and the reaction was stirred at room temperature for 15 minutes. 1N Sodium hydroxide (130 ml) was added and the reaction mixture was heated to 100° C. for 8 hours. The reaction mixture was cooled to room temperature and poured into a separatory funnel and washed with methyl t-butyl ether (2×200 ml). The aqueous layer was acidified to pH 1 with 6N hydrochloric acid and was extracted with ethyl acetate (150 ml). The solvent was removed under reduced pressure and to the resulting oil was added isopropyl alcohol (24 ml) and water (48 ml). A solid precipitated and the slurry was stirred 12 hours. The precipitate was filtered, washed with water, and dried to provide [6-chloro-2-(4-chloro-benzoyl)-1H-indol-3-yl]-acetic acid (9.73 g, 82%). mp 181-183° C. 1H NMR (400 MHz, d6-DMSO) d 3.79 (s, 2), 7.08 (dd, 1, J=8.5, 1.9), 7.42 (d, 1, J=1.9), 7.60 (d, 2, J=8.5), 7.62-7.73 (m, 3), 11.74 (bs, 1), 12.22 (bs, 1). 13C NMR (75 MHz, d6-DMSO) d 31.74, 113.25, 118.00, 121.93, 123.96, 127.69, 130.10, 131.30, 132.02, 133.59, 138.02, 138.37, 138.58, 173.20, 188.29. IR 3314, 1710, 1700, 1618, 1522, 1323, 1227, 1093, 941 cm−1. Analysis calculated for C17H11Cl2NO3: C, 58.64; H, 3.18; N, 4.02. Found: C, 58.58; H, 3.22; N, 3.93.

後処理

  1. temperaturethe reaction mixture was heated to 100° C. for 8 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. additionpoured into a separatory funnel
  4. washwashed with methyl t-butyl ether (2×200 ml)
  5. extractionwas extracted with ethyl acetate (150 ml)
  6. customThe solvent was removed under reduced pressure and to the resulting oil
  7. additionwas added isopropyl alcohol (24 ml) and water (48 ml)
  8. customA solid precipitated
  9. stirringthe slurry was stirred 12 hours
  10. filtrationThe precipitate was filtered
  11. washwashed with water
  12. customdried

出典と根拠

ORDレコード
ord-558cbae2079246d288c628255f0e9e66
出典データセット
uspto-grants-2003_08
特許番号
US06608070B1

反応ノート

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