Hydrochloric Acid → HCID 86759243, compound

HRID 479584Notes

Reaction equation

HRID 479584 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][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: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][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 76132,5-DimethoxyanilineHCID 18187381HCID 18187381, compound

Product 1

HCID 86759243HCID 86759243, compoundYield 72%

Procedure

A solution of 2,5-dimethoxyaniline (1.76 g, 11.49 mmol) and ethyl ∀-formylphenylacetate (2.43 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 isolated residue is crystallized from methanol and then filtered through a sinter funnel to give 2.71 g (72%) of compound 10.

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 through a sinter funnel

Sources & evidence

ORD record
ord-8bf18bea8a5644bab891d54fd7ac7e19
Source dataset
uspto-grants-2003_11
Patent number
US06645983B1

Reaction notes

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