Sulfuric Acid → 7-methoxy-6-nitro-1H-quinolin-2-one

HRID 1773561Notes

Reaction equation

HRID 1773561 reaction equation
S(=O)(=O)(O)O.C(O/[CH:9]=[CH:10]/[C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[C:16]([O:23][CH3:24])[CH:15]=1)=[O:12])C>>[CH3:24][O:23][C:16]1[CH:15]=[C:14]2[C:19]([CH:9]=[CH:10][C:11](=[O:12])[NH:13]2)=[CH:18][C:17]=1[N+:20]([O-:22])=[O:21]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 66664739(E)-3-ethoxy-N-(3-methoxy-4-nitro-phenyl)-acrylamide

Product 1

HCID 580563477-methoxy-6-nitro-1H-quinolin-2-oneYield 76.3%

Procedure

Concentrated sulfuric acid (1 mL) was added to (E)-3-ethoxy-N-(3-methoxy-4-nitro-phenyl)-acrylamide (225 mg) with cooling and the resulting mixture was stirred at room temperature for 1.5 hours. The reaction mixture was then poured into ice-water and stirred for 1 hour. The solid which crushed out was collected by filtration and dried under vacuum to give 142 mg of 7-methoxy-6-nitro-1H-quinolin-2-one as a brown solid. MS=221 [M+H]+.

Workup

  1. temperaturewith cooling
  2. stirringstirred for 1 hour
  3. customThe solid which crushed out
  4. filtrationwas collected by filtration
  5. customdried under vacuum

Sources & evidence

ORD record
ord-761a7f31c2f54b2bbe79af486723292c
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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