Acetyl chloride → 2-Acetyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

HRID 1958519노트

반응식

HRID 1958519 반응식
[OH-].[Na+].Cl.[CH2:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH:6]([C:14]([OH:16])=[O:15])[NH:5]1.[C:17](Cl)(=[O:19])[CH3:18]>CC(C)=O>[C:17]([N:5]1[CH:6]([C:14]([OH:16])=[O:15])[CH2:7][C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:4]1)(=[O:19])[CH3:18]

참가 물질

5

반응물 3

HCID 6367Acetyl chlorideHCID 14798Sodium Hydroxide2회HCID 27241351,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid hydrochloride

생성물 1

HCID 33051792-Acetyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

시약·촉매·용매 1

HCID 180Acetone용매2회

실험 절차

To a mixture of acetone (75 mL) and 2N NaOH (100 mL) was added portionwise 1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid hydrochloride (10.00 g, 46.8 mmol). After stirring for 10 min, acetyl chloride (7.38 g, 94 mmol) in acetone (50 mL) was added slowly into the above solution, followed with 2N NaOH at room temperature. The reaction mixture was maintained at a pH>10 and stirred for 1 hour. The acetone was evaporated in vacuo and acidified the residue by adding 3N HCl. The separated solid was collected by filtration, washed several times with water, and dried to afford the known 2-acetyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid as an enantiomeric mixture, 7.90 g, (76.9%); mp 178-180° C. (170-171° C.):21 1H NMR (DMSO-d6) δ 2.15 (3H, s, Me), 3.02-3.24 (2H, m), 4.29-4.75 (2H, m), 4.98-5.17 (1H, m), 7.17-7.21 (4H, m, 4×ArH), 12.70 (1H, brs, exchangeable, OH); m/z219.0 (M+H)+.

후처리

  1. temperatureThe reaction mixture was maintained at a pH>10
  2. stirringstirred for 1 hour
  3. customThe acetone was evaporated in vacuo
  4. additionby adding 3N HCl
  5. filtrationThe separated solid was collected by filtration
  6. washwashed several times with water
  7. customdried

출처 및 근거

ORD 기록
ord-84f3ee01b8f9457d8b256a815eb6038d
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410130B2

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