6-Nitro-2-oxo-1,2,3,4-tetrahydroquinolin-8-yl acetate → 8-Hydroxy-6-nitro-3,4-dihydroquinolin-2(1H)-one

HRID 1649000Notes

Reaction equation

HRID 1649000 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([O:14]C(=O)C)[CH:13]=1)[NH:10][C:9](=[O:18])[CH2:8][CH2:7]2)([O-:3])=[O:2]>Cl>[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([OH:14])[CH:13]=1)[NH:10][C:9](=[O:18])[CH2:8][CH2:7]2)([O-:3])=[O:2]

Participants

3

Reactant 1

HCID 131049106-Nitro-2-oxo-1,2,3,4-tetrahydroquinolin-8-yl acetate

Product 1

HCID 130510728-Hydroxy-6-nitro-3,4-dihydroquinolin-2(1H)-oneYield 82.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Hydrochloric acid (200 ml) was added to 6-nitro-8-acetoxy-3,4-dihydrocarbostyril (20 g) and the mixture was refluxed for 4 hours. After ice cooling, crystals which precipitated were collected by filtration and recrystallized from methanol to give 13.76 g of 6-nitro-8-hydroxy-3,4-dihydrocarbostyril.

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. customAfter ice cooling, crystals which precipitated
  3. filtrationwere collected by filtration
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-f024ccc9e3934d9c89138cedcea765d6
Source dataset
uspto-grants-1983_11
Patent number
US04414390

Reaction notes

Loading…