O-Toluidine → 4-(N-methylphenylamino)-2-(2-methylphenylamino)-6-methoxyquinazoline hydrochloride

HRID 973578Notes

Reaction equation

HRID 973578 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]([N:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:20][CH3:21])[CH:8]=2)[N:3]=1.[NH2:22][C:23]1[C:24]([CH3:29])=[CH:25][CH:26]=[CH:27][CH:28]=1.C(O)C.Cl>C(O)C>[ClH:1].[CH3:13][N:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:20][CH3:21])[CH:8]=2)[N:3]=[C:2]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:29])[N:11]=1

Participants

5

Reactant 3

HCID 7242O-ToluidineHCID 100861382-Chloro-4-(N-methylphenylamino)-6-methoxyquinazolineHCID 21887872Ethanol hydrochloride

Product 1

HCID 679259664-(N-methylphenylamino)-2-(2-methylphenylamino)-6-methoxyquinazoline hydrochlorideYield 57.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-chloro-4-(N-methylphenylamino)-6methoxyquinazoline (5.4 g, 0.027M), o-toluidine (4.28 g, 0.04M) in ethanol (50 ml) was heated in a Berchof pressure vessel at 140° for 5 hours (maximum pressure 40 psi). After cooling, ethanol/HCl was added and the solid which crystallised out was filtered off and recrystallised from isopropanol/ether to yield the title compound (4.23 g, m.p. 258°-260°).

Workup

  1. temperaturewas heated in a Berchof pressure vessel at 140° for 5 hours (maximum pressure 40 psi)
  2. temperatureAfter cooling
  3. customthe solid which crystallised out
  4. filtrationwas filtered off
  5. customrecrystallised from isopropanol/ether

Sources & evidence

ORD record
ord-f4874eb13583451e8289090777161ac8
Source dataset
uspto-grants-1991_11
Patent number
US05064833

Reaction notes

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