Stannous chloride dihydrate → 4-Hydrazino-5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid hydrochloride

HRID 1585277

Reaction equation

HRID 1585277 reaction equation
[N:1]([O-])=O.[Na+].[NH2:5][C:6]1[C:15]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[C:9]([C:16]([OH:18])=[O:17])=[CH:8][CH:7]=1.O.O.[Cl:21][Sn]Cl>O.Cl>[ClH:21].[NH:5]([C:6]1[C:15]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[C:9]([C:16]([OH:18])=[O:17])=[CH:8][CH:7]=1)[NH2:1]

Participants

6

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 221117984-Amino-5,6,7,8-tetrahydronaphthalene-1-carboxylic acidHCID 23668193Sodium Nitrite

Product 1

HCID 702454754-Hydrazino-5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid hydrochlorideYield 73.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
-5 °C

Procedure

A solution of 0.26 g of NaNO2 in 1 ml of water is added to a solution, cooled to -5° C., of 0.73 g of 4-amino-5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid in 10 ml of concentrated HCl. After one and a half hours of stirring at -5° C., a solution of 3.4 g of SnCl2.2H2O in 34 ml of concentrated HCl is added at -5° C. The mixture is stirred for 1 hour at RT and filtered, and the product is washed with concentrated HCl and dried under a stream of dry nitrogen to obtain 0.67 g of the expected hydrazine.

Workup

  1. stirringThe mixture is stirred for 1 hour at RT
  2. filtrationfiltered
  3. washthe product is washed with concentrated HCl
  4. customdried under a stream of dry nitrogen

Sources & evidence

ORD record
ord-1e10d0b2b31548f6ad392a9d63f74634
Source dataset
uspto-grants-1999_08
Patent number
US05936123

Linked notes

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