Acetyl chloride → HCID 13187734, compound

HRID 1719517Notes

Reaction equation

HRID 1719517 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)([O-])[O-].[Na+].[Na+].C(=O)(O)[O-].[Na+].[C:40](Cl)(=[O:42])[CH3:41]>C(Cl)(Cl)Cl.O1CCCC1>[C:26]([C:3]1([NH:2][C:40]([CH3:41])=[O:42])[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)(=[O:28])[CH3:27]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 20196338HCID 20196338, compound

Product 1

HCID 13187734HCID 13187734, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 9-amino-9-acetyl-6,7,11-trihydroxy-7,8,9,10-tetrahydro-5,12-naphthacenedione hydrochloride (130 mg), sodium carbonate (400 mg), a saturated sodium bicarbonate solution (20 ml), chloroform (10 ml) and tetrahydrofuran (10 ml) was stirred vigorously, and acetyl chloride (200 mg) was dropwise added thereto at room temperature. After the dropwise addition was completed, stirring was continued for 30 minutes. The reaction mixture was shaken with chloroform (50 ml). The chloroform layer was separated, washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue was recrystallized from diethyl ether to give 9-acetyl-9-acetamino-6,7,11-trihydroxy-7,8,9,10-tetrahydro-5,12-naphthacenedione. M.P., 240°-248° C.

Workup

  1. customat room temperature
  2. additionAfter the dropwise addition
  3. customThe chloroform layer was separated
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-839bed6e1ae7442589131d53036c480f
Source dataset
uspto-grants-1985_09
Patent number
US04540695

Reaction notes

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