HCID 46841135, compound → HCID 46841271, compound

HRID 1846319Notes

Reaction equation

HRID 1846319 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([C:12]2[N:21]([C:22]3[CH:27]=[CH:26][C:25]([NH:28]C(=O)C)=[CH:24][CH:23]=3)[C:20](=[O:32])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)=[CH:7][C:6]=1[CH3:33]>Cl>[NH2:28][C:25]1[CH:26]=[CH:27][C:22]([N:21]2[C:20](=[O:32])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=[C:12]2[C:8]2[CH:7]=[C:6]([CH3:33])[C:5]([O:4][CH2:3][CH2:2][OH:1])=[C:10]([CH3:11])[CH:9]=2)=[CH:23][CH:24]=1

Participants

3

Reactant 1

HCID 46841135HCID 46841135, compound

Product 1

HCID 46841271HCID 46841271, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of N-(4-(2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)-4-oxoquinazolin-3(4H)-yl)phenyl)acetamide (2.0 g, 4.50 mmol) in 2N HCl (50 mL) was stirred at reflux temperature for 30 minutes. The solids were filtered off solids and the aqueous filtrate was basified with NaOH, extracted with CH2Cl2, washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 2% to 10% MeOH in CH2Cl2, afforded 3-(4-aminophenyl)-2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)quinazolin-4(3H)-one as an off-white solid (1.35 g, 75%).

Workup

  1. temperatureat reflux temperature for 30 minutes
  2. filtrationThe solids were filtered off solids
  3. extractionextracted with CH2Cl2
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by flash chromatography on silica gel
  9. washeluting with 2% to 10% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-6b64628a5aeb45d89d2357a55e9c0682
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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