Hydrochloric Acid → HCID 86759242, compound

HRID 479583Notes

Reaction equation

HRID 479583 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][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:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH:6]/[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 108243-MethoxyanilineHCID 18187381HCID 18187381, compound

Product 1

HCID 86759242HCID 86759242, compoundYield 56%

Procedure

A solution of 3-methoxyaniline (1.55 ml, 13.79 mol) and ethyl ∀-formylphenylacetate (2.92 g, 1.1 eq) in toluene (20 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 2.30 g (56%) of compound 8 (Z isomer) in the form of a yellow 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-8df21636d25a4819bc535f9519c3b779
Source dataset
uspto-grants-2003_11
Patent number
US06645983B1

Reaction notes

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