Hydrochloric Acid → HCID 86759247, compound

HRID 479588Notes

Reaction equation

HRID 479588 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.[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:9]=[CH:8][C:6]([NH:7]/[CH:10]=[C:12](/[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)\[C:13]([O:15][CH2:25][CH3:26])=[O:14])=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1140Toluene2×HCID 7732P-AnisidineHCID 86759245HCID 86759245, compound

Product 1

HCID 86759247HCID 86759247, compoundYield 74%

Procedure

A solution of 4-methoxyaniline (1.47 g, 11.94 mmol) and ethyl ∀-formyl-4-methoxyphenylacetate (2.92 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 2.89 g (74%) of compound 22 (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-f3999e6d1576471a91432f153481aacd
Source dataset
uspto-grants-2003_11
Patent number
US06645983B1

Reaction notes

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