Sodium Dithionite → 4-Chloroquinazolin-6-amine

HRID 1068967Notes

Reaction equation

HRID 1068967 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-])=O)[CH:10]=2)[N:5]=[CH:4][N:3]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+]>O1CCCC1.O.CCOCC>[NH2:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][N:3]=[C:2]2[Cl:1]

Participants

6

Reactant 2

HCID 24489Sodium DithioniteHCID 113562574-Chloro-6-nitroquinazoline

Product 1

HCID 183506914-Chloroquinazolin-6-amine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture consisting of 3.25 g of 4-chloro-6-nitroquinazoline, 10.8 g of sodium hydrosulfite, and 0.3 g of the phase transfer catalyst (C8H17)3NCH3+Cl− in 97 mL of tetrahydrofuran and 32 mL of water was stirred rapidly for 2 hours. The mixture was diluted with ether and the organic layer was separated. The organic solution was washed with brine and then dried over magnesium sulfate. The solution was passed through a small column of silica gel. The solvent was removed at 30° C. at reduced pressure giving 6-amino-4-chloroquinazoline which is used in the next step without additional purification.

Workup

  1. customthe organic layer was separated
  2. washThe organic solution was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed at 30° C. at reduced pressure

Sources & evidence

ORD record
ord-534cf75621724cffa6ec9699ff0be416
Source dataset
uspto-grants-2001_06
Patent number
US06251912B1

Reaction notes

Loading…