4-Aminophenol → HCID 136160072, compound

HRID 392179Notes

Reaction equation

HRID 392179 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.[OH:16][C:17]1[CH:23]=[CH:22][C:20](N)=[CH:19][CH:18]=1.C([N:26](CC)CC)C>>[OH:16][C:17]1[CH:23]=[CH:22][C:20]([C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[C:4]([NH2:26])[N:3]=2)=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 4034-AminophenolHCID 8471TriethylamineHCID 27693644-Chloro-6,7-dimethoxyquinazoline

Product 1

HCID 136160072HCID 136160072, compound

Procedure

A mixture of 448 mg (2 mmol) of 4-chloro-6,7-dimethoxyquinazoline (7) and 2.5 mmol of 4-hydroxyaniline in 20 ml of alcohol (EtOH or MeOH) was refluxed for 8 hours. After cooling triethylamine was added to basify the solution, and the solvent was concentrated to give material that was recrystallized from DMF to give compound (1); 84.29%; m.p. 245.0-248.0° C.; 1H NMR (DMSO-d6): δ 11.21(s, 1H, —NH), 9.70(s, 1H, —OH), 8.74(s, 1H, 2-H), 8.22(s, 1H, 5-H), 7.40(d, 2H, J=8.9 Hz, 2′,6′-H), 7.29(s, 1H, 8-H), 6.85(d, 2H, J=8.9 Hz, 3′,5′-H), 3.98(s, 3H, —OCH3), 3.97(s, 3H, —OCH3). UV(MeOH) λmax(e): 203.0, 222.0, 251.0, 320.0 nm. IR(KBr)umax: 3428, 2836, 1635, 1516, 1443, 1234 cm−1.GC/MS m/z 298 (M++1, 100.00), 297(M+, 26.56), 296(M+−1, 12.46).

Workup

  1. temperaturewas refluxed for 8 hours
  2. additionwas added
  3. concentrationthe solvent was concentrated
  4. customto give material that
  5. customwas recrystallized from DMF

Sources & evidence

ORD record
ord-eadd79342d9a4d5185219b11795c6778
Source dataset
uspto-grants-2004_10
Patent number
US06800649B1

Reaction notes

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