HCID 18996993, compound → HCID 18996975, compound

HRID 374647Notes

Reaction equation

HRID 374647 reaction equation
C([NH:4][C:5](C(OCC)=O)([CH2:11][C:12]1[CH:25]=[C:24]([OH:26])[C:23]2[C:22](=[O:27])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][C:20]=3[OH:28])[C:15](=[O:29])[C:14]=2[CH:13]=1)[C:6]([O:8]CC)=[O:7])(=O)C>Br>[NH2:4][CH:5]([CH2:11][C:12]1[CH:25]=[C:24]([OH:26])[C:23]2[C:22](=[O:27])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][C:20]=3[OH:28])[C:15](=[O:29])[C:14]=2[CH:13]=1)[C:6]([OH:8])=[O:7]

Participants

3

Reactant 1

HCID 18996993HCID 18996993, compound

Product 1

HCID 18996975HCID 18996975, compound

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A mixture of ethyl 2-acetamido-2-carboethoxy-3-(9,10-dihydro-4,5-dihydroxy-9,10-dioxoanthracen-2-yl)propanoate (99.7 g) and 47% hydrobromic acid (1500 ml) was stirred at reflux for 6 hours. The mixture was cooled to room temperature and filtered. The isolated solid was stirred with 1N sodium hdroxide (1600 ml) for 15 minutes and the mixture filtered. The filtrate was cooled to 10° C. and acidified using glacial acetic acid (720 ml). The mixture was stirred for 10 minutes and then filtered. The isolated solid was washed with water (1 liter), pulled dry and then dried in vacuo at 60° C., m.p. 210°-212° C.

Workup

  1. temperatureat reflux for 6 hours
  2. filtrationfiltered
  3. stirringThe isolated solid was stirred with 1N sodium hdroxide (1600 ml) for 15 minutes
  4. filtrationthe mixture filtered
  5. temperatureThe filtrate was cooled to 10° C.
  6. stirringThe mixture was stirred for 10 minutes
  7. filtrationfiltered
  8. washThe isolated solid was washed with water (1 liter)
  9. custompulled dry
  10. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-dbc322f81da74f9dad2a9bba380c2137
Source dataset
uspto-grants-1996_01
Patent number
US05480873

Reaction notes

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