Triethylamine → methyl5,6-dihydro-5-oxo-11-H-indeno[1,2-c]isoquinoline-10-carboxylate

HRID 1642343

反応式

HRID 1642343 の反応式
Br[CH2:2][C:3]1[C:12]([C:13]#[N:14])=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].C1(=O)O[C:19](=[O:20])[C:18]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]2[CH2:16]1.C(N(CC)CC)C>C(#N)C>[O:20]=[C:19]1[C:18]2[C:17](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:16]2[CH2:2][C:3]3[C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]=2[NH:14]1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 12801Homophthalic anhydrideHCID 17837598Methyl 2-(bromomethyl)-3-cyanobenzoate

生成物 1

HCID 58772535methyl5,6-dihydro-5-oxo-11-H-indeno[1,2-c]isoquinoline-10-carboxylate収率 81%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

実験手順

A mixture of methyl 2-bromomethyl-3-cyanobenzoate (14.1 g, 55.5 mmol) and homophthalic anhydride (22.5 g, 138.8 mmol) in acetonitrile (150 mL) was stirred at room temperature. A solution of triethylamine (23.2 mL) in acetonitrile (100 mL) was added dropwise over the period of 1 hour. After the completion of addition, the resultant suspension was refluxed for 4 hours. The reaction mixture was then cooled to room temperature and filtered. The resultant solid was washed thoroughly with acetonitrile (100 mL) and ethanol (2×100 mL) and dried in vacuum oven at 50° C. to provide methyl 5,6-dihydro-5-oxo-11-H-indeno[1,2-c]isoquinoline-10-carboxylate was obtained in 81% yield (13.1 g). 1H NMR spectrum (in DMSO-d6): δ 12.21 (s, 1H); 8.20 (m, 2H); 7.83 (d, J=7.5 Hz, 1H); 7.71 (m, 2H); 7.47 (m, 2H); 4.07 (s, 2H); 3.89 (s, 3H).

後処理

  1. additionAfter the completion of addition
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. filtrationfiltered
  4. washThe resultant solid was washed thoroughly with acetonitrile (100 mL) and ethanol (2×100 mL)
  5. customdried in vacuum oven at 50° C.

出典と根拠

ORDレコード
ord-82260941896c4961bad159bfc6ae7c07
出典データセット
uspto-grants-2012_02
特許番号
US08119654B2

関連ノート

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