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

HRID 429023Notes

Reaction equation

HRID 429023 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-dc9ee7e0aea04fcf8753be698f850b28
Source dataset
uspto-grants-2001_11
Patent number
US06316203B1

Reaction notes

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