Sodium Carbonate → (4-Hydrazinophenyl)acetic acid hydrochloride

HRID 1517647Notes

Reaction equation

HRID 1517647 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[N:18]([O-])=O.[Na+].[Sn](Cl)[Cl:23]>O.Cl>[ClH:23].[NH:1]([C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:6][CH:7]=1)[NH2:18]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 145334-Aminophenylacetic acidHCID 24479Stannous ChlorideHCID 23668193Sodium Nitrite

Product 1

HCID 15618594(4-Hydrazinophenyl)acetic acid hydrochloride

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

15.1 g (10.0 mmol) 4-aminophenylacetic acid are placed in a solution of 10.6 g (10.0 mmol) sodium carbonate in 100 ml of water. The mixture is cooled to 0° C., then 6.9 g (10.0 mmol) sodium nitrite in 50 ml of water are added. This mixture is added dropwise to 100 ml of conc. hydrochloric acid while being cooled, then stirred for 0.1 hours. 45.1 g (20.0 mmol) tin(II)-chloride in 40 ml of conc. hydrochloric acid are added dropwise with vigorous stirring, during which time a precipitate is formed. The reaction mixture is stirred for 1 hour at ambient temperature, then suction filtered. The precipitate is washed with water and dried.

Workup

  1. temperaturewhile being cooled
  2. customis formed
  3. stirringThe reaction mixture is stirred for 1 hour at ambient temperature
  4. filtrationsuction filtered
  5. washThe precipitate is washed with water
  6. customdried

Sources & evidence

ORD record
ord-3921f977e77e45c29312d4f686212540
Source dataset
uspto-grants-2012_07
Patent number
US08232286B2

Reaction notes

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