Hydrochloric Acid → HCID 86759241, compound

HRID 479582Notes

Reaction equation

HRID 479582 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5].[CH:10]([CH:12]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:13]([O-:15])=[O:14])=O.Cl.[C:23]1(C)C=CC=C[CH:24]=1>>[CH3:1][O:2][C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH:5]/[CH:10]=[C:12](/[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)\[C:13]([O:15][CH2:23][CH3:24])=[O:14]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1140Toluene2×HCID 70002-MethoxyanilineHCID 18187381HCID 18187381, compound

Product 1

HCID 86759241HCID 86759241, compoundYield 68%

Procedure

A solution of 2-methoxyaniline (1.20 ml, 10.64 mmol) and ethyl ∀-formylphenylacetate (2.25 g, 1.1 eq) in toluene (20 ml ) is refluxed for 18 hours. After cooling, the reaction mixture is diluted with toluene (10 ml) and then acidified with 10% HCl. After extraction, the organic phase obtained is dried over MgSO4 and then evaporated under reduced pressure. The residue is purified by chromatography on a column of silica (eluent: CH2Cl2) to give 2.15 g (68%) of compound 3 (Z isomer) in the form of a yellow oil.

Workup

  1. temperatureAfter cooling
  2. extractionAfter extraction
  3. customthe organic phase obtained
  4. dry with materialis dried over MgSO4
  5. customevaporated under reduced pressure
  6. customThe residue is purified by chromatography on a column of silica (eluent: CH2Cl2)

Sources & evidence

ORD record
ord-6d3ed04e087d43c1a60018ec3443c72c
Source dataset
uspto-grants-2003_11
Patent number
US06645983B1

Reaction notes

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