Hydrazine hydrate (1:1) → Adenosine-5'-carboxylic acid hydrazide

HRID 27981Notes

Reaction equation

HRID 27981 reaction equation
C[O:2][C:3]([CH:5]([OH:23])[C@H:6]1[O:10][C@@H:9]([N:11]2[C:20]3[N:19]=[CH:18][N:17]=[C:15]([NH2:16])[C:14]=3[N:13]=[CH:12]2)[C@H:8]([OH:21])[C@@H:7]1[OH:22])=O.O.[NH2:25][NH2:26]>CO>[C@@H:9]1([N:11]2[C:20]3[N:19]=[CH:18][N:17]=[C:15]([NH2:16])[C:14]=3[N:13]=[CH:12]2)[O:10][C@H:6]([CH:5]([C:3]([NH:25][NH2:26])=[O:2])[OH:23])[C@@H:7]([OH:22])[C@H:8]1[OH:21]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 54489690Adenosine-5'-carboxylic acid methyl ester

Product 1

HCID 70580905Adenosine-5'-carboxylic acid hydrazideYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5 g of adenosine-5'-carboxylic acid methyl ester are suspended in 150 ml of methanol mixed with 20 ml of hydrazine hydrate and heated to the boil. The ester thereby goes into solution, while, almost simultaneously, the hydrazide precipitates out in the form of a fine crystalline material. After standing overnight, it is filtered off with suction, washed with methanol and dried. There are obtained 4.4 g of adenosine-5'-carboxylic acid hydrazide, which melts, with decomposition, at 270°-272° C. The yield is 93% of theory. The compound can be readily recrystallized from hot water.

Workup

  1. temperatureheated to the boil
  2. customwhile, almost simultaneously, the hydrazide precipitates out in the form of a fine crystalline material
  3. filtrationit is filtered off with suction
  4. washwashed with methanol
  5. customdried

Sources & evidence

ORD record
ord-73b107906a7646b28f6ccf1d187bcd96
Source dataset
uspto-grants-1980_09
Patent number
US04224438

Reaction notes

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