Nitric Acid → HCID 20072781, compound

HRID 704618Notes

Reaction equation

HRID 704618 reaction equation
[Cl: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.[N+:13]([O-])([OH:15])=[O:14]>C(OC(=O)C)(=O)C.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([N+:13]([O-:15])=[O:14])[CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 131049148-Chloro-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 20072781HCID 20072781, compoundYield 60.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Procedure

To a solution of 8-chloro-3,4-dihydro-2(1H)-quinolinone (5.08 g) in acetic anhydride (50 ml) was dropwise added a solution of nitric acid (d=1.40, 2.97 g) in acetic acid (20 ml) over the period of 10 minutes with stirring under ice-cooling. The mixture was stirred for 2 hours at ambient temperature and then for 6 hours at 50° C., and was allowed to stand for 60 hours at ambient temperature. The resulting precipitates were collected, washed with acetic anhydride and ethyl acetate successively and dried to give 8-chloro-6-nitro-3,4-dihydro-2(1H)-quinolinone (3.83 g).

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred for 2 hours at ambient temperature
  3. waitto stand for 60 hours at ambient temperature
  4. customThe resulting precipitates
  5. customwere collected
  6. washwashed with acetic anhydride and ethyl acetate successively
  7. customdried

Sources & evidence

ORD record
ord-271bbf43b1a34492b22ec1ab101bbf20
Source dataset
uspto-grants-1991_01
Patent number
US04988698

Reaction notes

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