Triethylamine → 3,4-Dihydro-N-methoxy-N-methyl-2(1H)-isoquinolinecarboxamide

HRID 361607

反応式

HRID 361607 の反応式
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[C:11](Cl)=[O:12].Cl.[CH3:15][NH:16][O:17][CH3:18].C(N(CC)CC)C.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:18][O:17][N:16]([CH3:15])[C:11]([N:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:1]1)=[O:12]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 218905713,4-Dihydroisoquinoline-2(1H)-carbonyl chloride

生成物 1

HCID 121859113,4-Dihydro-N-methoxy-N-methyl-2(1H)-isoquinolinecarboxamide収率 93.5%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

A solution of 2.73 g of 3,4-dihydro-1H-isoquinoline-2-carbonyl chloride, 55 mg of 4-dimethylamino-pyridine, 1.36 g of N,O-dimethylhydroxylamine hydrochloride and 4.85 ml of triethylamine in 30 ml of methylene chloride was heated to boiling under reflux for 22 h. The reaction mixture was treated at room temperature with 50 ml of a 5% sodium carbonate solution and extracted twice with 50 ml of methylene chloride each time. The combined organic phases were washed once with 50 ml of water and once with 50 ml of a saturated sodium chloride solution, dried over magnesium sulfate and concentrated. The residue was triturated with 50 ml of t-butyl methyl ether, a small amount of insoluble residue was filtered off under suction and the filtrate was concentrated. The residue was dried at room temperature and about 12 mbar. 2.87 g (93%) of 3,4-dihydro-1H-isoquinoline-2-carboxylic acid methoxy-methyl-amide were obtained as an orange oil. MS (EI): 220M30 .

後処理

  1. temperatureunder reflux for 22 h
  2. extractionextracted twice with 50 ml of methylene chloride each time
  3. washThe combined organic phases were washed once with 50 ml of water and once with 50 ml of a saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was triturated with 50 ml of t-butyl methyl ether
  7. filtrationa small amount of insoluble residue was filtered off under suction
  8. concentrationthe filtrate was concentrated
  9. customThe residue was dried at room temperature

出典と根拠

ORDレコード
ord-08c6d8c75ad94af08228b5173a998f86
出典データセット
uspto-grants-1999_02
特許番号
US05866583

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