Hydrochloric Acid → HCID 13491462, compound

HRID 1719519Notes

Reaction equation

HRID 1719519 reaction equation
[C:1]([C:4]1([NH:26]C(C)=O)[CH2:21][C:20]2[C:19]([OH:22])=[C:18]3[C:9]([C:10](=[O:24])[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=4[C:17]3=[O:23])=[C:8]([OH:25])[C:7]=2[CH2:6][CH2:5]1)(=[O:3])[CH3:2].Cl>C(O)(=O)C>[C:1]([C:4]1([NH2:26])[CH2:21][C:20]2[C:19]([OH:22])=[C:18]3[C:9]([C:10](=[O:24])[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=4[C:17]3=[O:23])=[C:8]([OH:25])[C:7]=2[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 13187707HCID 13187707, compound

Product 1

HCID 13491462HCID 13491462, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 9-acetyl-9-acetamino-6,11-dihydroxy-7,8,9,10-tetrahydro-5,12-naphthacenedione (3.0 g), acetic acid (90 ml) and conc. hydrochloric acid (60 ml) was heated under reflux for 9 hours. The reaction mixture was concentrated under reduced pressure. The residue was admixed with a saturated sodium bicarbonate solution (1000 ml), followed by stirring for 1 hour. The precipitated crystals were collected by filtration to give 9-acetyl-9-amino-6,11-dihydroxy-7,8,9,10-tetrahydro-5,12-naphthacenedione (2.6 g). M.P., 190°-195° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 9 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-a3a55eed33e04fd8847b82392135bf83
Source dataset
uspto-grants-1985_09
Patent number
US04540695

Reaction notes

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