Hydrochloric Acid → HCID 86759249, compound

HRID 479591Notes

Reaction equation

HRID 479591 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][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)[C:15]([O-:17])=[O:16])=O.Cl.[C:27]1(C)C=CC=C[CH:28]=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][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)\[C:15]([O:17][CH2:27][CH3:28])=[O:16]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1140Toluene2×HCID 227703,4-DimethoxyanilineHCID 86759245HCID 86759245, compound

Product 1

HCID 86759249HCID 86759249, compoundYield 65%

Procedure

A solution of 3,4-dimethoxyaniline (1.76 g, 11.49 mmol) and ethyl ∀-formyl-4-methoxyphenylacetate (2.81 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 silica gel (eluent: 7/3 PE/EtOAc) to give 2.67 g (65%) of compound 30 in the form of a pale yellow solid.

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 silica gel (eluent: 7/3 PE/EtOAc)

Sources & evidence

ORD record
ord-1e51f50f7ee9410d996b6dffe28cefcf
Source dataset
uspto-grants-2003_11
Patent number
US06645983B1

Reaction notes

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