delta-Gluconolactone → (4-(Benzyloxy)phenyl)hydrazine monohydrochloride

HRID 1655829Notes

Reaction equation

HRID 1655829 reaction equation
[CH2:1]([O:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:16]([O-])=O.[Na+].O.O.[Sn](Cl)[Cl:23].C(O)[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O>Cl.O.C(O)C>[ClH:23].[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([NH:13][NH2:16])=[CH:14][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 7027delta-GluconolactoneHCID 228604-BenzyloxyanilineHCID 61436Stannous chloride dihydrateHCID 23668193Sodium Nitrite

Product 1

HCID 3016725(4-(Benzyloxy)phenyl)hydrazine monohydrochlorideYield 89%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolvent3×HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
-2 °C

Procedure

To a slurry of 4-benzyloxyaniline (250 g) and ethanol 300 ml) in 30% HCl (350 ml) and 37% HCl (150 ml) was added a solution of sodium nitrite (77 g) in water (350 ml), while maintaining the temperature between -8 and -2° C. The reaction was stirred for an additional four hours at -2° C. A solution of tin (II) chloride dihydrate (710 g) in 30% HCl (770 ml) was added slowly followed by d-gluconic acid lactone (575 g), and the resulting white suspension was cooled overnight. The crude product was collected by vacuum filtration and washed with 1 N hydrochloric acid, ether, and vacuum dried to give 248.9 g of the desired product, m.p. 173-174° C.

Workup

  1. temperaturewhile maintaining the temperature between -8 and -2° C
  2. temperaturethe resulting white suspension was cooled overnight
  3. filtrationThe crude product was collected by vacuum filtration
  4. washwashed with 1 N hydrochloric acid, ether, and vacuum
  5. customdried

Sources & evidence

ORD record
ord-8b7da48cfb2b40878a559da82bb39f23
Source dataset
uspto-grants-1993_10
Patent number
US05252426

Reaction notes

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