Ammonium formate → 4-(6,7-Dimethoxy-2-methyl-quinazolinyloxy)-phenylamine

HRID 705680Notes

Reaction equation

HRID 705680 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[C:8]([CH3:15])[N:7]=[C:6]2OC1C=CC([N+]([O-])=O)=CC=1.[CH:26]([O-:28])=O.[NH4+:29]>CCO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[NH:9][C:8]([CH3:15])([O:28][C:26]1[CH:5]=[CH:4][C:3]([NH2:29])=[CH:12][CH:11]=1)[N:7]=[CH:6]2

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 666694296,7-Dimethoxy-2-methyl-4-(4-nitro-phenoxy)-quinazoline

Product 1

HCID 693308904-(6,7-Dimethoxy-2-methyl-quinazolinyloxy)-phenylamineYield 2,499%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 6,7-dimethoxy-2-methyl-4-(4-nitro-phenoxy)quinazoline (0.081 g, 0.236 mmole), Pt/S (0.008 g, 15 mol %), ammonium formate (0.098 g, 1.56 mmol) and EtOH (3 mL) was heated with stirring at 70° C. for 3 hours. The reaction mixture was then filtered while hot and washed with hot EtOH. The crude product of 4-(6,7-dimethoxy-2-methyl-quinazolinyloxy)-phenylamine (0.924 g) was obtained as a yellow solid, which was used in the next reaction without further purification. LC/MS: m/z 312 (M+H).

Workup

  1. temperaturewas heated
  2. filtrationThe reaction mixture was then filtered while hot and
  3. washwashed with hot EtOH

Sources & evidence

ORD record
ord-48c9775bbaff4373a8a37d349bc66409
Source dataset
uspto-grants-2015_11
Patent number
US09174947B2

Reaction notes

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