Hydrochloric Acid → 8-Methoxy-2-(4-methoxy-phenylamino)-4-phenylamino-quinazoline dihydrochloride

HRID 50537Notes

Reaction equation

HRID 50537 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]2[C:4](=[C:5]([O:19][CH3:20])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:21][O:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1.[ClH:30]>C(O)(C)C.O1CCOCC1>[ClH:1].[ClH:30].[CH3:20][O:19][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([NH:27][C:26]1[CH:28]=[CH:29][C:23]([O:22][CH3:21])=[CH:24][CH:25]=1)[N:11]=[C:10]2[NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7732P-AnisidineHCID 226398112-Chloro-8-methoxy-4-phenylamino-quinazoline

Product 1

HCID 226398198-Methoxy-2-(4-methoxy-phenylamino)-4-phenylamino-quinazoline dihydrochloride

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-chloro-8-methoxy-4-phenylamino-quinazoline (1.20 g) and 4-methoxy-aniline (0.66 g) is heated for 3 min to produce a melt which is dissolved in isopropanol (15 ml). 4N HCl in dioxane (0.2 ml) is added. Crystallization from isopropanol and diethylether yields 8-methoxy-2-(4-methoxy-phenylamino)-4-phenylamino-quinazoline dihydrochloride, m.p. 287-289° C., FAB-MS: (M+H)+=373. Analytical data: C22H20N4O2+HCl.

Workup

  1. temperatureis heated for 3 min
  2. customto produce a melt which
  3. customCrystallization from isopropanol and diethylether

Sources & evidence

ORD record
ord-b6f552188fe343b4928cc28ad65bdcde
Source dataset
uspto-grants-2004_03
Patent number
US06713265B1

Reaction notes

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