Hydrochloric Acid → 5-Amino-2-methylthio-4-(3-aminophenyl)-quinazoline-6-carboxylic acid

HRID 1435711Notes

Reaction equation

HRID 1435711 reaction equation
[NH2:1][C:2]1[C:11]([C:12]([O-:14])=[O:13])=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([NH2:23])[CH:18]=1)=[N:5][C:6]([S:15][CH3:16])=[N:7]2.[OH-].[K+].Cl>O1CCOCC1>[NH2:1][C:2]1[C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([NH2:23])[CH:18]=1)=[N:5][C:6]([S:15][CH3:16])=[N:7]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 211090795-Amino-2-methylthio-4-(3-aminophenyl)-quinazoline-6-carboxylate

Product 1

HCID 211090805-Amino-2-methylthio-4-(3-aminophenyl)-quinazoline-6-carboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 5-amino-2-methylthio-4-(3-aminophenyl)-quinazoline-6-carboxylate (example 27f, 658 mg) in 1,4-dioxane was treated with an aqueous solution of KOH (2 M, 4.2 ml) at 70° C. for 18 h. After the reaction mixture was cooled to room temperature, it was acidified to pH 1 with 4 N HCl. The mixture was extracted with CH2Cl2 (3×). The combined organic layers were dried (MgSO4) and concentrated under reduced pressure to give the crude title compound.

Workup

  1. extractionThe mixture was extracted with CH2Cl2 (3×)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d3f0ce977d374f65baa09c06fd8089ff
Source dataset
uspto-grants-2009_11
Patent number
US07618963B2

Reaction notes

Loading…