5-Amino-2-methylphenol → HCID 22478272, compound

HRID 547172Notes

Reaction equation

HRID 547172 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+:16]([O-:18])=[O:17])=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][NH:7][C:6]2=O.S(Cl)([Cl:21])=O.[OH:23][C:24]1[CH:25]=[C:26]([CH:28]=[CH:29][C:30]=1[CH3:31])[NH2:27]>CN(C=O)C.CC(O)C>[ClH:21].[CH3:1][O:2][C:3]1[C:4]([N+:16]([O-:18])=[O:17])=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[NH:27][C:26]1[CH:28]=[CH:29][C:30]([CH3:31])=[C:24]([OH:23])[CH:25]=1

Participants

6

Reactant 3

HCID 178185-Amino-2-methylphenolHCID 24386Thionyl ChlorideHCID 135513647HCID 135513647, compound

Product 1

HCID 22478272HCID 22478272, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of 6,7-dimethoxy-5-nitro-3,4-dihydroquinazolin-4-one (1.75 g, 7.0 mmol) and thionyl chloride (25 ml) and DMF (3 drops) was heated at reflux for 2 hours. Excess thionyl chloride was removed by evaporation and the residue azeotroped with toluene. 3-Hydroxy-4-methylaniline (0.94 g, 7.6 mmol) in 2-propanol (40 ml) was added to the residue and the mixture heated at reflux for 2 hours. The mixture was allowed to cool, the precipitate collected by filtration, washed with 2-propanol and dried to give 6,7-dimethoxy-4-(3-hydroxy-4-methylanilino)-5-nitroquinazoline hydrochloride (2.02 g, 81%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. customExcess thionyl chloride was removed by evaporation
  4. customthe residue azeotroped with toluene
  5. temperaturethe mixture heated
  6. temperatureat reflux for 2 hours
  7. temperatureto cool
  8. filtrationthe precipitate collected by filtration
  9. washwashed with 2-propanol
  10. customdried

Sources & evidence

ORD record
ord-ea67b57407444abd995e8b20ff64996d
Source dataset
uspto-grants-2011_05
Patent number
USRE042353E1

Reaction notes

Loading…