Daunorubicin Hydrochloride → Daunorubicin

HRID 1703941Notes

Reaction equation

HRID 1703941 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.C1(C2C=CC(C(NN)=O)=CC=2)C=CC=CC=1>CO>[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

4

Reactant 2

HCID 62770Daunorubicin HydrochlorideHCID 72718p-Phenylbenzhydrazide

Product 1

HCID 30323DaunorubicinYield 111.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.13 g (2.0 mmole) of daunomycin hydrochloride and 0.85 g (4.0 mmole) of 4-phenylbenzhydrazide in 75 ml of methanol was stirred at room temperature in the dark for 4 days. After concentrating to about 10 ml, the reaction mixture was stirred and slowly diluted with 100 ml of acetonitrile. The resulting precipitate was collected and washed with 3 × 5 ml of acetonitrile to afford 1.174 g of the hydrazone (I) with a small amount of 4-phenylbenzhydrazide. The mother liquors were evaporated; the residue was dissolved in 5 ml of methanol and the stirred solution was diluted with 75 ml of acetonitrile to give an additional 0.211 g of (I). The two crops of (I) were combined and dissolved in 5 ml of methanol; the solution was stirred and 75 ml of acetonitrile were added dropwise. The resulting precipitate was triturated in the methanol-acetonitrile mixture overnight and then collected, washed with acetonitrile and dried at room temperature/0.1 mm/15 hr to yield the hydrazone hydrochloride (I), 1.253 g (81%) mp 205°-208° decomposed.

Workup

  1. concentrationAfter concentrating to about 10 ml
  2. additionslowly diluted with 100 ml of acetonitrile
  3. customThe resulting precipitate was collected
  4. washwashed with 3 × 5 ml of acetonitrile

Sources & evidence

ORD record
ord-ad62024268224c8d916ae96891917c00
Source dataset
uspto-grants-1978_11
Patent number
US04125704

Reaction notes

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