Stannous chloride dihydrate → 4-Hydrazino-3-methoxybenzoic acid hydrochloride

HRID 582765

Reaction equation

HRID 582765 reaction equation
[N:1]([O-])=O.[Na+].[NH2:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][C:7]=1[O:15][CH3:16].O.O.[Cl:19][Sn]Cl>O.Cl>[ClH:19].[NH:5]([C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][C:7]=1[O:15][CH3:16])[NH2:1]

Participants

6

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 2880572486-69-3HCID 23668193Sodium Nitrite

Product 1

HCID 702454494-Hydrazino-3-methoxybenzoic acid hydrochloride

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 2.17 g of NaNO2 in 40 ml of H2O is added slowly to a solution, cooled to 0° C., of 5 g of 4-amino-3-methoxybenzoic acid in 50 ml of concentrated HCl. After 1 hour 15 minutes of stirring at 0° C., the mixture is cooled to -10° C., and a solution of 23.6 g of SnCl2.2H2O in 20 ml of concentrated HCl and 20 ml of water is added over 30 min. After one and a half hours of stirring at -10° C., the mixture is filtered, and the precipitate is washed with 50 ml of pentane to obtain, after drying, 6 g of expected product.

Workup

  1. temperaturethe mixture is cooled to -10° C.
  2. stirringAfter one and a half hours of stirring at -10° C.
  3. filtrationthe mixture is filtered
  4. washthe precipitate is washed with 50 ml of pentane
  5. customto obtain
  6. customafter drying

Sources & evidence

ORD record
ord-58a34facecef405c803051203acc39dc
Source dataset
uspto-grants-1999_07
Patent number
US05925661

Linked notes

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