Hydrochloric Acid → HCID 57810258, compound

HRID 705611Notes

Reaction equation

HRID 705611 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-8687d83963084de89dcb46bdde8429fa
Source dataset
uspto-grants-2015_11
Patent number
US09174947B2

Reaction notes

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