Acetic Acid → HCID 22732301, compound

HRID 2084006Notes

Reaction equation

HRID 2084006 reaction equation
[CH3:1][C:2]1[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][C:3]=1[NH:4][C:5]1[C:14]2[C:9](=[C:10](OC)[C:11]([O:17][CH3:18])=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]=[CH:7][N:6]=1.C(O)C.C(O)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>O>[NH2:25][C:22]1[CH:23]=[CH:24][C:2]([CH3:1])=[C:3]([CH:21]=1)[NH:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:17][CH3:18])=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]=[CH:7][N:6]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 10340Sodium CarbonateHCID 22732273HCID 22732273, compound

Product 1

HCID 22732301HCID 22732301, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Using similar procedures to those described in the last paragraph of the portion of Example 2 which is concerned with the preparation of starting materials, a solution of 4-(2-methyl-5-nitroanilino)-6,7,8-trimethoxyquinazoline in a 30:3:1 mixture of ethanol, acetic acid and water was reduced at 90° C. during 18 hours. Solid sodium carbonate was added after cooling. The filtrate was triturated with diethyl ether and the resultant residue was purified by column chromatography eluting with 2.5% methanol in ethyl acetate to give 4-(5-amino-2-methylanilino)-6,7-dimethoxyquinazoline; NMR: (CDCl3) 2.73 (s, 3H), 3.95 (s, 3H), 4.04 (s, 3H), 4.14 (s, 3H), 6.9 (s, 1H), 7.21 (m, 2H), 7.64 (s, 1H), 7.96 (d, 1H), 8.50 (s, 1H), 8.72 (s, 1H); Mass: M+H+ 341.

Workup

  1. customis concerned with the preparation of starting materials
  2. temperatureafter cooling
  3. customThe filtrate was triturated with diethyl ether
  4. customthe resultant residue was purified by column chromatography
  5. washeluting with 2.5% methanol in ethyl acetate

Sources & evidence

ORD record
ord-99ab4d50558f43469a3261c9bcd00340
Source dataset
uspto-grants-2004_04
Patent number
US06716847B2

Reaction notes

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