Semicarbazide hydrochloride → 2,3-Dihydroxy-naphthaldehyde semicarbazone

HRID 745564Notes

Reaction equation

HRID 745564 reaction equation
Cl.[NH2:2][NH:3][C:4]([NH2:6])=[O:5].C([O-])(=O)C.[Na+].[OH:12][C:13]1[C:22]([OH:23])=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]=1[CH:24]=O>O.CO>[OH:12][C:13]1[C:22]([OH:23])=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]=1[CH:24]=[N:2][NH:3][C:4]([NH2:6])=[O:5]

Participants

6

Reactant 3

HCID 11236Semicarbazide hydrochlorideHCID 517045Sodium AcetateHCID 133438102,3-Dihydroxy-1-naphthaldehyde

Product 1

HCID 1359884562,3-Dihydroxy-naphthaldehyde semicarbazoneYield 73.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
10 °C

Procedure

86.0 g of semicarbazide hydrochloride dissolved in 500 ml of water and 103 g of sodium acetate (CH3COONa.3H2O) were placed in a 2.5 l sulfonation flask equipped with stirrer, thermometer and dropping funnel. At an internal temperature of 40°-50° C., there was added dropwise a solution of 138.4 g of 2,3-dihydroxy-naphthaldehyde in 1000 ml of methanol. The mixture was stirred at 40°-50° C. for 1 hour and then, after adding 2 l of water, cooled to 10° C. and suction filtered. The material on the suction filter was back-washed thoroughly with water and dried at 60° C. in vacuo. Recrystallization from glacial acetic acid gave 131.9 g (73.1% of theory) of 2,3-dihydroxy-naphthaldehyde semicarbazone of melting point 210°-215° C.

Workup

  1. customequipped with stirrer
  2. filtrationsuction filtered
  3. filtrationThe material on the suction filter
  4. washwas back-washed thoroughly with water
  5. customdried at 60° C. in vacuo
  6. customRecrystallization from glacial acetic acid

Sources & evidence

ORD record
ord-41bc2b663bed424ba4d6f6fae9066953
Source dataset
uspto-grants-1986_07
Patent number
US04599347

Reaction notes

Loading…