Hydrochloric Acid → HCID 15507787, compound

HRID 479589Notes

Reaction equation

HRID 479589 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].[CH:10]([CH:12]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)[C:13]([O-:15])=[O:14])=O.Cl.[C:25]1(C)C=CC=C[CH:26]=1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH:6]/[CH:10]=[C:12](/[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)\[C:13]([O:15][CH2:25][CH3:26])=[O:14]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1140Toluene2×HCID 108243-MethoxyanilineHCID 86759245HCID 86759245, compound

Product 1

HCID 15507787HCID 15507787, compoundYield 70%

Procedure

A solution of 3-methoxyaniline (1.75 ml, 15.57 mmol) and ethyl ∀-formyl-4-methoxyphenylacetate (3.81 g), 1.1 eq) in toluene (25 ml) is refluxed for 18 hours. After cooling, the reaction mixture is diluted with toluene (15 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 3.57 g (70%) of compound 25 (Z isomer) in the form of a white solid which crystallizes from methanol.

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-dbaf68ec47d44589807928a69a8937c1
Source dataset
uspto-grants-2003_11
Patent number
US06645983B1

Reaction notes

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