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

HRID 1958519ノート

反応式

HRID 1958519 の反応式
[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]

参加物

5

反応物 3

HCID 6367Acetyl chlorideHCID 14798Sodium Hydroxide2 回HCID 27241351,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid hydrochloride

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒2 回

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-84f3ee01b8f9457d8b256a815eb6038d
出典データセット
uspto-grants-2013_04
特許番号
US08410130B2

反応ノート

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