Hydrochloric Acid → HCID 19592334, compound

HRID 613536Notes

Reaction equation

HRID 613536 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[NH:12][CH:11]=[CH:10][C:9]2=O)([O-:3])=[O:2].[O:15]1[CH2:20]OCOC1.[ClH:21]>O1CCOCC1>[Cl:21][CH2:9][C:10]1[C:20](=[O:15])[C:8]2[C:13](=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][CH:7]=2)[NH:12][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 80811,3,5-TrioxaneHCID 2885428-Nitroquinolin-4-ol

Product 1

HCID 19592334HCID 19592334, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 1,4-dihydro-8-nitro-4-oxoquinoline (10 g) and 1,3,5-trioxane (23.7 g) in dioxane (100 ml) and conc. hydrochloric acid (200 ml) was stirred for 3.5 hours at 90° C. and allowed to stand to ambient temperature. To the mixture was added ice water (700 g), and the mixture was stirred for 1 hour. The resulting precipitates were collected by filtration and washed with cold water to give 3-chloromethyl-1,4-dihydro-8-nitro-4-oxoquinoline (6.5 g).

Workup

  1. customto stand to ambient temperature
  2. stirringthe mixture was stirred for 1 hour
  3. customThe resulting precipitates
  4. filtrationwere collected by filtration
  5. washwashed with cold water

Sources & evidence

ORD record
ord-c1ff41a89d4147abb7ab6262ee9c9edd
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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