Daunorubicin Hydrochloride → Daunorubicin

HRID 1703942Notes

Reaction equation

HRID 1703942 reaction equation
[CH3:1][C@@H:2]1[O:7][C@@H:6]([O:8][C@@H:9]2[C:18]3[C:13](=[C:14]([OH:32])[C:15]4[C:24](=[O:25])[C:23]5[CH:26]=[CH:27][CH:28]=[C:29]([O:30][CH3:31])[C:22]=5[C:20](=[O:21])[C:16]=4[C:17]=3[OH:19])[CH2:12][C@@:11]([OH:36])([C:33]([CH3:35])=[O:34])[CH2:10]2)[CH2:5][C@H:4]([NH2:37])[C@@H:3]1[OH:38].Cl.ClC1C=C(C=CC=1Cl)C(NN)=O>CO.C(#N)C>[CH3:1][C@@H:2]1[O:7][C@@H:6]([O:8][C@@H:9]2[C:18]3[C:13](=[C:14]([OH:32])[C:15]4[C:24](=[O:25])[C:23]5[CH:26]=[CH:27][CH:28]=[C:29]([O:30][CH3:31])[C:22]=5[C:20](=[O:21])[C:16]=4[C:17]=3[OH:19])[CH2:12][C@@:11]([OH:36])([C:33]([CH3:35])=[O:34])[CH2:10]2)[CH2:5][C@H:4]([NH2:37])[C@@H:3]1[OH:38]

Participants

5

Reactant 2

HCID 62770Daunorubicin HydrochlorideHCID 3119963,4-Dichlorobenzhydrazide

Product 1

HCID 30323DaunorubicinYield 117.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 0.564 g (1.0 mmole) of daunomycin hydrochloride and 0.410 g (2.0 mmole) of 3,4-dichlorobenzhydrazide in 20 ml of methanol was stirred at room temperature in the dark for 3 days. The reaction mixture was stirred and slowly diluted with 100 ml of acetonitrile; the clear solution was allowed to stand at room temperature in the dark overnight. The resulting precipitate was collected, washed with 5 × 1 ml of methanol-acetronitrile (1:5) and dried at room temperature/0.1 mm/16 hr to give 0.619 g (82%) of the hydrazone (III), mp 249°-251° decomposed.

Workup

  1. customto stand at room temperature in the dark overnight
  2. customThe resulting precipitate was collected
  3. washwashed with 5 × 1 ml of methanol-acetronitrile (1:5)
  4. customdried at room temperature/0.1 mm/16 hr

Sources & evidence

ORD record
ord-aa5bc5a831d343819d90ba8d84ba4dde
Source dataset
uspto-grants-1978_11
Patent number
US04125704

Reaction notes

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