Malic Acid → 7-Diethylaminocoumarin

HRID 2072270Notes

Reaction equation

HRID 2072270 reaction equation
[CH2:1]([N:3]([CH2:11][CH3:12])[C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)[CH3:2].C(O)(=O)[CH:14]([CH2:16][C:17](O)=O)[OH:15].S(=O)(=O)(O)O.CN(C)C1C=C2C(C=CC(=O)O2)=CC=1>>[CH2:11]([N:3]([CH2:1][CH3:2])[C:4]1[CH:5]=[C:6]2[C:7]([CH:17]=[CH:16][C:14](=[O:15])[O:10]2)=[CH:8][CH:9]=1)[CH3:12]

Participants

5

Reactant 4

HCID 525Malic AcidHCID 1118Sulfuric AcidHCID 70623-(Diethylamino)phenolHCID 115357057-Dimethylaminocoumarin

Product 1

HCID 885987-Diethylaminocoumarin

Procedure

m-Diethylaminophenol 7.4g, malic acid 6.0g and 85% sulfuric acid 12.0ml were treated as for the 7-dimethylamino-coumarin, although the alumina column cut could not be induced to crystallize. It was rechromatographed, eluting first with benzene thoroughly, and then developing with dichloromethane. After two crystallizations from cyclohexane, cream colored crystals 0.5g (5%), m.p. 87.5°-88.0° were obtained, found C 71.94; H 7.09; N 6.35; C13H15NO2 requires C 7.19; H 6.92; N 6.45%.

Workup

  1. customto crystallize
  2. customIt was rechromatographed
  3. washeluting first with benzene thoroughly
  4. customAfter two crystallizations from cyclohexane, cream colored crystals 0.5g (5%)
  5. customm.p. 87.5°-88.0° were obtained

Sources & evidence

ORD record
ord-22f7f12acb484929a9e62aef11ce9cbd
Source dataset
uspto-grants-1977_09
Patent number
US04051062

Reaction notes

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