HCID 14501787, compound → HCID 13934988, compound

HRID 231412Notes

Reaction equation

HRID 231412 reaction equation
[NH2:1][C:2]1[C:3]([Cl:18])=[CH:4][C:5]([Cl:17])=[C:6]([CH2:8][N:9]2[C:13](=[O:14])[C:12]([CH3:16])([CH3:15])[CH2:11][O:10]2)[CH:7]=1.[N:19]([O-])=O.[Na+]>Cl.O>[ClH:17].[Cl:18][C:3]1[CH:4]=[C:5]([Cl:17])[C:6]([CH2:8][N:9]2[C:13](=[O:14])[C:12]([CH3:16])([CH3:15])[CH2:11][O:10]2)=[CH:7][C:2]=1[NH:1][NH2:19]

Participants

5

Reactant 2

HCID 14501787HCID 14501787, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 13934988HCID 13934988, compoundYield 10.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-[(5-amino-2,4-dichlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone (16.3 g, 0.564 mole) in concentrated hydrochloric acid (75 ml) was cooled to 0° C., and a solution of sodium nitrite (3.9 g, 0.564 mole) in water (50 ml) was added dropwise with the tip of the addition funnel below the surface of the solution. The reaction mixture temperature was kept below 2° C. during the addition. Upon completion of addition, the reaction mixture was stirred at 0° C. for 30 minutes, and then stannous chloride (28 g, 0.124 mole) in concentrated hydrochloric acid (50 ml) was added dropwise maintaining the temperature below 2° C. The reaction mixture was stirred for one hour at 0° C., and then a tan solid was removed by filtration to yield 10.0 g of [2,4-dichloro-5-[(4,4-dimethyl-3-oxoisoxazolidin-2-yl)methyl]phenyl]hydrazine hydrochloride; m.p. 202°-205° C.

Workup

  1. additionThe reaction mixture temperature was kept below 2° C. during the addition
  2. additionUpon completion of addition
  3. temperaturemaintaining the temperature below 2° C
  4. stirringThe reaction mixture was stirred for one hour at 0° C.
  5. customa tan solid was removed by filtration

Sources & evidence

ORD record
ord-8f0a7fbaf2504bdb8a21db08c851099d
Source dataset
uspto-grants-1989_07
Patent number
US04846875

Reaction notes

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