5,12-Naphthacenedione, 8-acetyl-7,8,9,10-tetrahydro-6,8,11-trihydroxy- → 9-Bromoacetyl-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydronaphthacene-5,12-dione

HRID 464007Notes

Reaction equation

HRID 464007 reaction equation
[C:1]([C:4]1([OH: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].C1CNC(=O)C1.[Br:33][Br-]Br>O1CCCC1>[Br:33][CH2:2][C:1]([C:4]1([OH: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]

Participants

3

Reactant 1

HCID 111217035,12-Naphthacenedione, 8-acetyl-7,8,9,10-tetrahydro-6,8,11-trihydroxy-

Product 1

HCID 131462669-Bromoacetyl-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydronaphthacene-5,12-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Reaction of 9-acetyl-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydronaphthacene-5,12-dione (352 mg) with pyrrolidone hydrotribromide (562 mg) was effected in tetrahydrofuran (50 ml) at room temperature for 40 hours. After removing insoluble materials by filtration, the filtrate was concentrated under reduced pressure to give 9-bromoacetyl-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydronaphthacene-5,12-dione, which was used in the next step without purification.

Workup

  1. customAfter removing insoluble materials
  2. filtrationby filtration
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-677f758ea124492193a7577adb342f62
Source dataset
uspto-grants-1985_10
Patent number
US04545936

Reaction notes

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