Aniline → 2-Chloro-8-methoxy-4-phenylamino-quinazoline

HRID 50538Notes

Reaction equation

HRID 50538 reaction equation
[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]2[C:4](=[C:5]([O:13][CH3:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(N(CC)C(C)C)(C)C.[NH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(O)(C)C>[Cl:1][C:2]1[N:11]=[C:10]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:9]2[C:4](=[C:5]([O:13][CH3:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 81531DiisopropylethylamineHCID 104213312,4-Dichloro-8-methoxyquinazoline

Product 1

HCID 226398112-Chloro-8-methoxy-4-phenylamino-quinazoline

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 2,4-dichloro-8-methoxy-quinazoline (prepared as described in J. Chem. Soc. 1948, 1759) (0.6 g), N,N-diisopropyl-ethylamine (0.87 ml), and aniline (0.26 ml) in isopropanol (10 ml) is heated to reflux for 45 min. The cold reaction mixture is filtered and residue is crystallized from dichloromethane and hexanes to give 2-chloro-8-methoxy-4-phenylamino-quinazoline, m.p. 245-246° C.

Workup

  1. temperatureto reflux for 45 min
  2. customThe cold reaction mixture
  3. filtrationis filtered
  4. customresidue is crystallized from dichloromethane and hexanes

Sources & evidence

ORD record
ord-b9cfe957a94744fca732a14ad8d8c0d8
Source dataset
uspto-grants-2004_03
Patent number
US06713265B1

Reaction notes

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