Hydrochloric Acid → HCID 10613943, compound

HRID 479586Notes

Reaction equation

HRID 479586 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:8]([CH:10]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[C:11]([O-:13])=[O:12])=O.Cl.[C:23]1(C)C=CC=C[CH:24]=1>>[NH:1](/[CH:8]=[C:10](/[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)\[C:11]([O:13][CH2:23][CH3:24])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1140Toluene2×HCID 6115AnilineHCID 86759245HCID 86759245, compound

Product 1

HCID 10613943HCID 10613943, compoundYield 71%

Procedure

A solution of aniline (1.85 ml, 20.30 mmol) and ethyl ∀-formyl-4-methoxyphenylacetate (4.96 g, 1.1 eq) in toluene (15 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: 4/6 PE/CH2Cl2) to give 4.29 g (71%) of compound 18 (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: 4/6 PE/CH2Cl2)

Sources & evidence

ORD record
ord-3f124082f5ed4e4cb694132bce174035
Source dataset
uspto-grants-2003_11
Patent number
US06645983B1

Reaction notes

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