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

HRID 1642343

반응식

HRID 1642343 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

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).

후처리

  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.

출처 및 근거

ORD 기록
ord-82260941896c4961bad159bfc6ae7c07
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08119654B2

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