Hydrochloric Acid → HCID 57810258, compound

HRID 562972Notes

Reaction equation

HRID 562972 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[F:16][C:17]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:18]=1[NH2:26].Cl>C(C#N)(C)=O>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][N:3]=[C:2]2[NH:26][C:18]1[CH:19]=[CH:20][C:21]([N+:23]([O-:25])=[O:24])=[CH:22][C:17]=1[F:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1012542-Fluoro-4-nitroanilineHCID 27693644-Chloro-6,7-dimethoxyquinazoline

Product 1

HCID 57810258HCID 57810258, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 694302-OxopropiononitrileSolvent

Procedure

A mixture of 4-chloro-6,7-dimethoxy-quinazoline (548 mg, 2.4 mmol), 2-fluoro-4-nitro-phenylamine (392 mg, 2.5 mmol), AcCN (10 ml), and conc'd HCl (0.050 ml) was heated to reflux for several hrs. After the reaction mixture was allowed to cool to room temperature, the resulting solids were filtered, washed with AcCN and air-dried to give (6,7-dimethoxy-quinazolin-4-yl)-(2-fluoro-4-nitro-phenyl)-amine (673 mgs, 80%). 1H-NMR (400 MHz, DMSO): 12.18 (br s, 1H), 8.91 (s, 1H), 8.45 (s, 1H), 8.36 (dd, 1H), 8.24 (dd, 1H), 7.91 (dd, 1H), 7.44 (s, 1H), 4.04 (s, 3H), 4.02 (s, 3H). LC/MS Calcd for [M+H]+ 345.1, found 345.4.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for several hrs
  3. filtrationthe resulting solids were filtered
  4. washwashed with AcCN
  5. customair-dried

Sources & evidence

ORD record
ord-43d6cb3af20b4986b60697046626c939
Source dataset
uspto-grants-2011_11
Patent number
US08067436B2

Reaction notes

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