Water → ethyl 8-bromo-2,2-dimethyl-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylate

HRID 1168507Notes

Reaction equation

HRID 1168507 reaction equation
[CH3:1][C:2]1([CH3:20])[N:12]2[C:13]3[C:8]([C:9](=[O:19])[C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:11]2)=[CH:7][CH:6]=[CH:5][C:4]=3[CH2:3]1.[Br:21]Br.O>C(O)(=O)C>[Br:21][C:6]1[CH:7]=[C:8]2[C:13]3=[C:4]([CH2:3][C:2]([CH3:1])([CH3:20])[N:12]3[CH:11]=[C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:9]2=[O:19])[CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 12083031HCID 12083031, compound

Product 1

HCID 12083032ethyl 8-bromo-2,2-dimethyl-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylateYield 38%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ethyl 2,2-dimethyl-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylate (Preparation 12, 1.03 g) is dissolved in acetic acid (10 mL) and bromine (213 μL) is added dropwise. The reaction is stirred an additional 30 min and then poured into water (50 mL). The resulting precipitate is filtered and then washed with ether to give 506 mg (38%) of the title compound as white crystals. Physical characteristics: M.p. 227-228° C.; 1H NMR (DMSO-d6) δ8.76, 7.90, 7.79, 4.23, 3.41, 1.63, 1.29; IR (diffuse reflectance) 1727, 1636, 1612, 1592, 1547, 1505, 1393, 1373, 1327, 1303, 1217, 1171, 1167, 1128, 804 cm−1; HRMS (FAB) 350.0386 (C16H16BrNO3+H).

Workup

  1. filtrationThe resulting precipitate is filtered
  2. washwashed with ether

Sources & evidence

ORD record
ord-c5bac66b8c1448fb87dd3bf4d669ec2a
Source dataset
uspto-grants-2003_09
Patent number
US06624159B2

Reaction notes

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