Ethyl Acetate → HCID 11579998, compound

HRID 2381007Notes

Reaction equation

HRID 2381007 reaction equation
[CH3:1][C:2]1[N:11]=[C:10]([N:12]([C:14]2[CH:19]=[CH:18][C:17]([N:20](C)[C:21](=O)C)=[CH:16][CH:15]=2)[CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(OCC)(=O)C>CO.[OH-].[Na+]>[CH3:1][C:2]1[N:11]=[C:10]([N:12]([C:14]2[CH:15]=[CH:16][C:17]([NH:20][CH3:21])=[CH:18][CH:19]=2)[CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 11638343HCID 11638343, compound

Product 1

HCID 11579998HCID 11579998, compoundYield 31.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of (2-methyl-quinazolin-4-yl)-(N-methyl-4-acetamido-phenyl)-methylamine (103 mg, 0.321 mmol) in 3 mL of methanol and 3 mL of 2N NaOH was heated at 90° C. for 4 h. The reaction mixture was cooled to room temperature and diluted 25 mL of ethyl acetate. It was washed with saturated NaHCO3, and the organic layer was dried over anhydrous Na2SO4, filtered and concentrated. The crude was purified by column chromatography (40% ethyl acetate/hexane) to give the title compound (28 mg, 0.10 mmol, 31%). 1H NMR (CDCl3): 7.71 (m, 1H), 7.50 (ddd, J=8.4, 6.9, 1.5, 1H), 6.93-7.11 (m, 4H), 6.60 (m, 2H), 3.84 (s, broad, 1H), 3.57 (s, 3H), 2.87 (s, 3H), 2.70 (s, 3H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washIt was washed with saturated NaHCO3
  3. dry with materialthe organic layer was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude was purified by column chromatography (40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a3d827bc57d04e4cbd3ea86168ca2d5b
Source dataset
uspto-grants-2012_09
Patent number
US08258145B2

Reaction notes

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