Acetic Acid → 5-Hydroxy-6-Nitro-3,4-Dihydrocarbostyril

HRID 622332Notes

Reaction equation

HRID 622332 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=[O:12])[NH:7]2.[N+:13]([O-])([OH:15])=[O:14].C(O)(=O)C>C(OC(=O)C)(=O)C>[OH:1][C:2]1[C:11]([N+:13]([O-:15])=[O:14])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=[O:12])[NH:7]2

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 944Nitric AcidHCID 1691533,4-Dihydro-5-hydroxy-2(1H)-quinolinone

Product 1

HCID 142738595-Hydroxy-6-Nitro-3,4-DihydrocarbostyrilYield 69%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
5 °C

Procedure

In 110 ml of acetic anhydride was dissovled 25 g of 5-hydroxy-3,4-dihydrocarbostyril, and to the solution was added dropwise a mixture of 12 g of fuming nitric acid and 75 ml of acetic acid at 5° C. After stirring at 5° C. for 2 hours, 20 g of ice was added to the reaction mixture, and the precipitated crystals were collected. The crystals were suspended in a 3N sodium hydroxide aqueous solution, followed by filtration. The filtrate was neutralized with hydrochloric acid, and the precipitated crystals were collected by filtration, washed with water, and dried to obtain 22 g of the named compound.

Workup

  1. additionto the solution was added dropwise
  2. customthe precipitated crystals were collected
  3. filtrationfollowed by filtration
  4. filtrationthe precipitated crystals were collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-d124ebbd5a6d484099c4869bc2e8f587
Source dataset
uspto-grants-1988_09
Patent number
US04770988

Reaction notes

Loading…