Ammonia → 4-Oxo-4,5-dihydrothieno[3,2-c]quinoline-7-carboxamide

HRID 2174906Notes

Reaction equation

HRID 2174906 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]([O:17]C)=O)=[CH:5][C:4]=2[NH:3]1.[OH-].[Na+].[NH3:21]>>[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]([NH2:21])=[O:17])=[CH:5][C:4]=2[NH:3]1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 14798Sodium HydroxideHCID 50941659HCID 50941659, compound

Product 1

HCID 509417554-Oxo-4,5-dihydrothieno[3,2-c]quinoline-7-carboxamideYield 32%

Conditions

Temperature
100 °C

Procedure

In a closed vessel, Methyl 4-oxo-4,5-dihydrothieno[3,2-c]quinoline-7-carboxylate (44 mg, 0.170 mmol) was suspended in concentrated aqueous ammonia (1 ml). The mixture was stirred at 100° C. overnight. Aqueous 1N NaOH was added and the mixture stirred at room temperature for 2 hours. The solid was filtered and dried to provide 4-oxo-4,5-dihydrothieno[3,2-c]quinoline-7-carboxamide as a brown solid (13 mg, 32% yield). LCMS (ES): 95% pure, m/z 245 [M+1]+.

Workup

  1. stirringthe mixture stirred at room temperature for 2 hours
  2. filtrationThe solid was filtered
  3. customdried

Sources & evidence

ORD record
ord-267bcca99450416b8a0c7fbaf596baa9
Source dataset
uspto-grants-2015_06
Patent number
US09062043B2

Reaction notes

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