Hydrochloric Acid → HCID 178486867, compound

HRID 1968653Notes

Reaction equation

HRID 1968653 reaction equation
[Na].F[C:3]1[CH:12]=[C:11]2[C:6]([C:7]([OH:13])=[N:8][CH:9]=[N:10]2)=[CH:5][C:4]=1[N+:14]([O-:16])=[O:15].Cl.[CH3:18][OH:19]>>[CH3:18][O:19][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([OH:13])=[N:8][CH:9]=[N:10]2)=[CH:5][C:4]=1[N+:14]([O-:16])=[O:15]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 5360545SodiumHCID 178526403HCID 178526403, compound

Product 1

HCID 178486867HCID 178486867, compoundYield 92%

Procedure

Sodium (92 mg, 4 mmol) was dissolved in methanol (4 mL) under nitrogen at 0° C. 7-Fluoro-6-nitroquinazolin-4-ol (418 mg, 2 mmol) was added. The mixture was refluxed for 3 h and cooled to room temperature and treated with 2N HCl to adjust its pH to 3-4. After the mixture was concentrated, the residue was diluted with ethyl acetate and washed with water twice. The organic layer was concentrated to give 405 mg (92%) of 7-methoxy-6-nitroquinazolin-4-ol.

Workup

  1. temperatureThe mixture was refluxed for 3 h
  2. concentrationAfter the mixture was concentrated
  3. additionthe residue was diluted with ethyl acetate
  4. washwashed with water twice
  5. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-8da124f63a1c425cb1f4d5227cb0d0af
Source dataset
uspto-grants-2013_04
Patent number
US08426430B2

Reaction notes

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