Water → 2-Bromo-4-oxo-4,5-dihydrothieno[3,2-c]quinoline-7-carbonitrile

HRID 1919676Notes

Reaction equation

HRID 1919676 reaction equation
[O:1]=[C:2]1[C:11]2[CH:12]=[CH:13][S:14][C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([C:15]#[N:16])=[CH:5][C:4]=2[NH:3]1.[Br:17]N1C(=O)CCC1=O.O>C(O)(=O)C>[Br:17][C:13]1[S:14][C:10]2[C:9]3[CH:8]=[CH:7][C:6]([C:15]#[N:16])=[CH:5][C:4]=3[NH:3][C:2](=[O:1])[C:11]=2[CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimide2×HCID 50941660HCID 50941660, compound

Product 1

HCID 575006912-Bromo-4-oxo-4,5-dihydrothieno[3,2-c]quinoline-7-carbonitrileYield 84%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

4-oxo-4,5-dihydrothieno[3,2-c]quinoline-7-carbonitrile (1.0 eq, 350 mg, 1.55 mmol) was mixed with N-bromosuccinimide (1.1 eq, 303 mg, 1.70 mmol) in acetic acid (4 ml). The mixture was stirred at 100° C. for 4 hours. The mixture was cooled down to 80° C., more NBS (303 mg) was added and the mixture stirred overnight. Water was added and the material filtered and dried. Trituration in methanol and filtration afforded 2-bromo-4-oxo-4,5-dihydrothieno[3,2-c]quinoline-7-carbonitrile as a grey solid (396 mg, 84% yield). LCMS (ES)>80% pure, m/z 305 [M]+, 307 [M+2]+.

Workup

  1. temperatureThe mixture was cooled down to 80° C.
  2. stirringthe mixture stirred overnight
  3. filtrationthe material filtered
  4. customdried
  5. filtrationTrituration in methanol and filtration

Sources & evidence

ORD record
ord-a0ac42475f4e4611b593af103d41323d
Source dataset
uspto-grants-2012_05
Patent number
US08168651B2

Reaction notes

Loading…