Hydrochloric Acid → HCID 86759248, compound

HRID 479590Notes

Reaction equation

HRID 479590 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:4]=1[NH2:5].[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:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:4]=1[NH:5]/[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 76132,5-DimethoxyanilineHCID 86759245HCID 86759245, compound

Product 1

HCID 86759248HCID 86759248, compoundYield 52%

Procedure

A solution of 2,5-dimethoxyaniline (1.07 g, 7.00 mmol) and ethyl ∀-formyl-4-methoxyphenylacetate (1.71 g, 1.1 eq) in toluene (15 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 isolated residue is crystallized from methanol and then filtered on a sinter funnel to give 1.30 g (52%) of compound 28.

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 isolated residue is crystallized from methanol
  7. filtrationfiltered on a sinter funnel

Sources & evidence

ORD record
ord-86a418f00b2d468eb41cbc6f51a61551
Source dataset
uspto-grants-2003_11
Patent number
US06645983B1

Reaction notes

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