Hydrochloric Acid → 2-Benzoyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

HRID 617779노트

반응식

HRID 617779 반응식
Cl.[CH2:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH:4]([C:12]([OH:14])=[O:13])[NH:3]1.[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl>[OH-].[Na+]>[C:15]([N:3]1[CH:4]([C:12]([OH:14])=[O:13])[CH2:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:2]1)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 27241351,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid hydrochloride

생성물 1

HCID 5700052-Benzoyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

시약·촉매·용매 1

HCID 14798Sodium Hydroxide용매

실험 절차

This compound was prepared according to Hein et. al., J. Amer. Chem. Soc.; 1962, 84, 4487-4494, incorporated by reference herein in its entirety. Thus, a slurry of 1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid hydrochloride (20.3 g, 95 mmol) in 2N NaOH (150 ml) was treated with benzoyl chloride (13.4 ml, 114 mmol) dropwise over 30 minutes. The mixture was stirred a further 1.5 hours, acidified to pH 2-3 (4N HCl), and extracted with ethyl acetate. The organic phase was washed with water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated to afford 16.4 g (61) of the title compound following recrystallization (acetone/water); MS: 280 m/z (M-H)-.

후처리

  1. customThis compound was prepared
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford
  8. custom16.4 g (61) of the title compound following recrystallization (acetone/water)

출처 및 근거

ORD 기록
ord-b8b70703deac4ded93d5efb4e749d480
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05952328

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