Acetic Acid → 6-Nitro-2-oxo-1,2,3,4-tetrahydroquinolin-8-yl acetate

HRID 1648999Notes

Reaction equation

HRID 1648999 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2.[C:13]([OH:16])(=O)[CH3:14].[N+:17]([O-])([OH:19])=[O:18]>C(OC(=O)C)(=O)C.S(=O)(=O)(O)O>[N+:17]([C:4]1[CH:5]=[C:6]2[C:11](=[C:2]([O:1][C:13](=[O:16])[CH3:14])[CH:3]=1)[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2)([O-:19])=[O:18]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 944Nitric AcidHCID 2682398-Hydroxy-3,4-dihydroquinolin-2(1h)-one

Product 1

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

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 7918Acetic AnhydrideSolvent2×

Conditions

Temperature
80 °C

Procedure

8-Hydroxy-3,4-dihydrocarbostyril (20 g) was suspended in acetic anhydride (100 ml). Sulfuric acid (5 drops) was added to the resulting suspension and the mixture was stirred at 80° C. for 1.5 hours. To the reaction mixture was added acetic acid (100 ml) and the mixture was ice-cooled, and a solution of 10.1 ml of concentrated nitric acid (d=1.38) in 30 ml of acetic anhydride was added thereto with stirring. The stirring was continued for one night at room temperature. The reaction mixture was poured into ice water to precipitate crystals, which were collected by filtration to give 21.74 g of 6-nitro-8-acetoxy-3,4-dihydrocarbostyril.

Workup

  1. temperaturecooled
  2. stirringwith stirring
  3. waitThe stirring was continued for one night at room temperature
  4. customto precipitate crystals, which
  5. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-15d72c0b072f47a4bec58c2027296a9b
Source dataset
uspto-grants-1983_11
Patent number
US04414390

Reaction notes

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