Hydrochloric Acid → HCID 13187727, compound

HRID 1719518Notes

Reaction equation

HRID 1719518 reaction equation
Cl.[NH2:2][C:3]1([C:26](=[O:28])[CH3:27])[CH2:20][C:19]2[C:18]([OH:21])=[C:17]3[C:8]([C:9](=[O:23])[C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=4[C:16]3=[O:22])=[C:7]([OH:24])[C:6]=2[CH:5]([OH:25])[CH2:4]1.C(O[C:33](=[O:35])[CH3:34])(=O)C.Cl>N1C=CC=CC=1>[C:26]([C:3]1([NH:2][C:33]([CH3:34])=[O:35])[CH2:20][C:19]2[C:18]([O:21][C:18](=[O:21])[CH3:17])=[C:17]3[C:8]([C:9](=[O:23])[C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=4[C:16]3=[O:22])=[C:7]([O:24][C:16](=[O:22])[CH3:15])[C:6]=2[CH:5]([O:25][C:9](=[O:23])[CH3:8])[CH2:4]1)(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 20196338HCID 20196338, compound

Product 1

HCID 13187727HCID 13187727, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 9-amino-9-acetyl-6,7,11-trihydroxy-7,8,9,10-tetrahydro-5,12-naphthacenedione hydrochloride (550 mg) and anhydrous pyridine (10 ml), acetic anhydride (3 ml) was added thereto while cooling with ice water. The resultant mixture was heated at a temperature of 60° to 65° C. for 30 minutes. The reaction mixture was poured into 3% hydrochloric acid and extracted with chloroform. The chloroform extract was washed with water, a saturated sodium bicarbonate solution and water in order, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by chromatography to give 9-acetyl-9-acetamino-6,7,11-triacetoxy-7,8,9,10-tetrahydro-5,12-naphthacenedione. M.P., 276°-278° C.

Workup

  1. additionwas added
  2. extractionextracted with chloroform
  3. extractionThe chloroform extract
  4. washwas washed with water
  5. dry with materiala saturated sodium bicarbonate solution and water in order, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-cf4d3cd436b347e7a263a8bb7bcd2cb4
Source dataset
uspto-grants-1985_09
Patent number
US04540695

Reaction notes

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