Hydrochloric Acid → HCID 23043629, compound

HRID 2165100Notes

Reaction equation

HRID 2165100 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C([Li])CCC.[Cl:25][C:26]1[CH:27]=[CH:28][C:29]([OH:39])=[C:30]([C:32](=[O:38])[C:33](OCC)=[O:34])[CH:31]=1.Cl>ClCCl.O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([NH:19][C:33](=[O:34])[C:32](=[O:38])[C:30]3[CH:31]=[C:26]([Cl:25])[CH:27]=[CH:28][C:29]=3[OH:39])=[CH:17][CH:18]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 142560244-(3,4-Dimethoxyphenethyl)anilineHCID 23043600HCID 23043600, compoundHCID 178418339Butyllithium

Product 1

HCID 23043629HCID 23043629, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Under an argon atmosphere, a tetrahydrofuran (20 ml) solution of 4-[2-(3,4-dimethoxyphenyl)ethyl]benzenamine (2.50 g, 9.72 mmol) is cooled to 0° C. n-Butyllithium (2.3M, 4.2 ml, 9.72 mmol) is added, and the resulting solution is stirred for 15 minutes. A tetrahydrofuran (10 ml) solution of ethyl 5-chloro-2-hydroxy-α-oxobenzenacetate (0.74 g, 3.24 mmol) is then added, after which the solution is allowed to warm to ambient temperature over a 30 minute period. The contents are then poured into 5% hydrochloric acid (100 ml) and extracted into ethyl acetate. The organics are washed with 10% sodium bicarbonate and brine, then dried (sodium sulfate), and concentrated to give 1.51 g of a crude solid. Chromatography (Kieselgel 60, dichloromethane) affords N-[4-[2-(3,4-dimethoxyphenyl)ethyl]phenyl]-2-hydroxy-5-chloro-α-oxobenzeneacetamide (0.86 g, 61%), mp 128°-130° C.

Workup

  1. additionis added
  2. extractionextracted into ethyl acetate
  3. washThe organics are washed with 10% sodium bicarbonate and brine
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated
  6. customto give 1.51 g of a crude solid

Sources & evidence

ORD record
ord-56faec66f0a840028921b5af3a140ae2
Source dataset
uspto-grants-1990_07
Patent number
US04939133

Reaction notes

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