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

HRID 130312

Reaction equation

HRID 130312 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

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, and a solution of triethylamine (23.2 ml) in acetonitrile (100 ml) was added dropwise to the mixture over the period of 1 h. After the completion of addition, the resultant suspension was refluxed for 4 hours. The reaction mixture was then cooled down to room temperature and filtered. The filtered solid was washed thoroughly with acetonitrile (100 ml) and ethanol (2×100 ml) and dried under vacuum at 50° C. Compound 17a was obtained in 81% yield (13.1 g). 1H NMR (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).

Workup

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

Sources & evidence

ORD record
ord-61e4851e636a4997b23c97e39043acd9
Source dataset
uspto-grants-2008_06
Patent number
US07381722B2

Linked notes

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