Diphenyl Ether → HCID 178469576, compound

HRID 1067951Notes

Reaction equation

HRID 1067951 reaction equation
[C:1]([O:4][CH2:5][CH2:6][N:7]([CH2:27][CH3:28])[C:8]1[CH:26]=[CH:25][C:11]([NH:12][CH:13]=[C:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]([O:17]CC)=O)=[CH:10][CH:9]=1)(=[O:3])[CH3:2].C1(OC2C=CC=CC=2)C=CC=CC=1>C(OCC)C>[C:1]([O:4][CH2:5][CH2:6][N:7]([CH2:27][CH3:28])[C:8]1[CH:9]=[C:10]2[C:11](=[CH:25][CH:26]=1)[N:12]=[CH:13][C:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:15]2[OH:17])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7583Diphenyl EtherHCID 21192536HCID 21192536, compound

Product 1

HCID 178469576HCID 178469576, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a flask containing crude diethyl 2-({4-[[2-(acetyloxy)ethyl](ethyl)amino]-anilino}methylene)malonate (2.2 g) is added diphenyl ether (15 mL). The reaction mixture is heated from room temperature to 260° C. over 45 minutes under a flow of argon gas. After 1 hour at 260° C. the hot reaction is slowly and carefully added to stirred diethyl ether (150 mL). The resulting precipitate is filtered and washed repeatedly with heptane. The residue is adsorbed onto silica and chromatographed on silica eluting with 3% to 10% methanol in dichloromethane. The product-containing fractions are evaporated to give 0.68 g of ethyl 6-[[2-(acetyloxy)ethyl](ethyl)amino]-4-hydroxy-3-quinolinecarboxylate as a brown solid.

Workup

  1. temperatureThe reaction mixture is heated from room temperature to 260° C. over 45 minutes under a flow of argon gas
  2. customAfter 1 hour at 260° C. the hot reaction
  3. additioncarefully added
  4. filtrationThe resulting precipitate is filtered
  5. washwashed repeatedly with heptane
  6. customchromatographed on silica eluting with 3% to 10% methanol in dichloromethane
  7. customThe product-containing fractions are evaporated

Sources & evidence

ORD record
ord-cab9f9ef06ae4cff802faea31eef25dc
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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