Water → HCID 17755114, compound

HRID 491686Notes

Reaction equation

HRID 491686 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]=[CH:8][N:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([N+:23]([O-])=O)[CH:17]=1.O>Cl.[Fe].CCO>[NH2:23][C:18]1[CH:17]=[C:16]([O:15][C:6]2[C:5]3[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=3)[N:9]=[CH:8][N:7]=2)[CH:21]=[CH:20][C:19]=1[OH:22]

Participants

6

Reactant 2

HCID 962WaterHCID 17755015HCID 17755015, compound

Product 1

HCID 17755114HCID 17755114, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

4-(6,7-Dimethoxyquinazolin-4-yloxy)-2-nitrophenol (Step c, 350 mg, 1.02 mmol) was combined with Fe (1.17 g), 6N HCl (2 drops), water (2.1 mL) and EtOH (9 mL) and heated at reflux for 2.5 h. The hot mixture was filtered through Celite and evaporated. The residue was purified by column chromatography using 0-30% of a 90:10:1 (CH2Cl2:MeOH:NH4OH) solution in CH2Cl2 as the eluent. MS(MH+)=NA; Calc'd 313.31 for C16H15N3O4.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2.5 h
  3. filtrationThe hot mixture was filtered through Celite
  4. customevaporated
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-6087d8c7bf4349baa230d8e8a7a9dc3f
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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