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

HRID 1739640Notes

Reaction equation

HRID 1739640 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-c9d8d395f3fe495692f65bbb0106cbe4
Source dataset
uspto-grants-1999_10
Patent number
US05968819

Reaction notes

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