Ethyl Acetate → HCID 13371473, compound

HRID 1719425Notes

Reaction equation

HRID 1719425 reaction equation
C[Li].[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:19]=2C(O)=O)=[CH:13][CH:12]=1)C1C=CC=CC=1.C([O:32][CH2:33][CH3:34])(=O)C.[Cl-].[NH4+]>O1CCCC1>[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:19]=2[C:33](=[O:32])[CH3:34])=[CH:13][CH:12]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 133714622-[4-(Benzyloxy)anilino]-5-methoxybenzoic acidHCID 178418348HCID 178418348, compound

Product 1

HCID 13371473HCID 13371473, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyllithium (210 ml, 1.25M methyllithium-lithium bromide complex in ether) (0.263 mole) was added dropwise to a solution of 25.49 g (0.0732 mole) of 2-(4-benzyloxyphenylamino)-5-methoxybenzoic acid in 226 ml of tetrahydrofuran cooled to 0°-5° C. The reaction mixture was stirred for 3 hours at 0°-5° C. Ethyl acetate was then added and the mixture poured into ice and saturated ammonium chloride solution. The aqueous suspension was extracted with ether, the ether extracts dried over anhydrous magnesium sulfate and concentrated. The residue was recrystallized from toluene to give 16.1 g of 1-[2-(4-benzyloxyphenylamino)-5-methoxyphenyl]ethanone, yellow-orange solid, m.p. 80°-81.5° C.

Workup

  1. temperaturecooled to 0°-5° C
  2. extractionThe aqueous suspension was extracted with ether
  3. dry with materialthe ether extracts dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was recrystallized from toluene

Sources & evidence

ORD record
ord-dc8de321cc2146fd9bc16873a16e433c
Source dataset
uspto-grants-1985_09
Patent number
US04539429

Reaction notes

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