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

HRID 396421노트

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HRID 396421 반응식
C[O:2][C:3](=[O:24])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:15](=[O:23])[C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1.[OH-].[Na+]>CO.C1COCC1>[Cl:14][C:10]1[CH:9]=[C:8]2[C:13]([C:5]([CH2:4][C:3]([OH:24])=[O:2])=[C:6]([C:15](=[O:23])[C:16]3[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=3)[NH:7]2)=[CH:12][CH:11]=1

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 9906983HCID 9906983, 화합물

생성물 1

HCID 9798374(6-chloro-2-(4-chlorobenzoyl)-1H-indol-3-yl)acetic acid수율 91.3%

시약·촉매·용매 1

HCID 21899815MeOH tetrahydrofuran용매

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온도
80 °C

실험 절차

A mixture of methyl[6-chloro-2-(4-chlorobenzoyl)-1H-indol-3-yl]acetate (Example 8, 1.80 g) and 2N aqueous NaOH (7.5 ml) in MeOH-THF (10 ml-10 ml) was stirred at 80° C. for 1 h. The mixture was cooled and concentrated. The residue was dissolved in water (150 ml) and washed with diethyl ether (50 ml). The aqueous layer was acidified with 2N aqueous HCl (10 ml), and extracted with ethyl acetate (100 ml×2). The combined organic extracts were washed with brine (50 ml), dried (MgSO4), and concentrated. The residual solids were recrystalized from toluene to afford 1.58 g (91%) of the title compound.

후처리

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in water (150 ml)
  4. washwashed with diethyl ether (50 ml)
  5. extractionextracted with ethyl acetate (100 ml×2)
  6. washThe combined organic extracts were washed with brine (50 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customThe residual solids were recrystalized from toluene

출처 및 근거

ORD 기록
ord-e3f5642825574b27b621e57f37b843da
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06608070B1

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