Hydrochloric Acid → HCID 86759244, compound

HRID 479585Notes

Reaction equation

HRID 479585 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[NH2:6].[CH:12]([CH:14]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:15]([O-:17])=[O:16])=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][C:9]=1[O:10][CH3:11])[NH:6]/[CH:12]=[C:14](/[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)\[C:15]([O:17][CH2:25][CH3:26])=[O:16]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1140Toluene2×HCID 227703,4-DimethoxyanilineHCID 18187381HCID 18187381, compound

Product 1

HCID 86759244HCID 86759244, compoundYield 60%

Procedure

A solution of 3,4-dimethoxyaniline (1.50 g, 9.79 mmol) and ethyl ∀-formylphenylacetate (2.07 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 1.92 g (60%) of compound 13 in the form of an oil 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-c065176d2ab54dbea5b83d35e092583a
Source dataset
uspto-grants-2003_11
Patent number
US06645983B1

Reaction notes

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