Ethanol → [4-(4-Chlorophenoxy)-3-nitrophenyl]hydrazine

HRID 840725Notes

Reaction equation

HRID 840725 reaction equation
[N:1]([O-])=O.[Na+].[Cl:5][C:6]1[CH:22]=[CH:21][C:9]([O:10][C:11]2[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][C:12]=2[N+:18]([O-:20])=[O:19])=[CH:8][CH:7]=1.C(O)C.O.O.[Sn](Cl)Cl>O.Cl>[Cl:5][C:6]1[CH:22]=[CH:21][C:9]([O:10][C:11]2[CH:17]=[CH:16][C:14]([NH:15][NH2:1])=[CH:13][C:12]=2[N+:18]([O-:20])=[O:19])=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 61436Stannous chloride dihydrateHCID 155801494-(4-Chlorophenoxy)-3-nitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 22620231[4-(4-Chlorophenoxy)-3-nitrophenyl]hydrazine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 0.52 g of sodium nitrite in 5 ml of water was added dropwise to a stirred mixture consisting of 1.9 g of 4-(4-chlorophenoxy)-3-nitroaniline, 25 ml of concentrated hydrochloric acid and 25 ml of ethanol cooled to 0° C., and the mixture was then stirred at 0° C. for 60 min and subsequently added dropwise to a suspension of 8.5 g of tin dichloride dihydrate in 8 ml of concentrated HCl. The precipitate was filtered off with suction, washed with water, suspended in 200 ml of water under nitrogen and decomposed with 100 ml of 30% strength sodium hydroxide solution at 10-15° C. The oil formed was extracted by shaking with ethyl acetate and washed with water, and the organic phase was dried with sodium sulfate. The product was then precipitated with isopropanolic HCl, filtered off with suction and dried in vacuo.

Workup

  1. filtrationThe precipitate was filtered off with suction
  2. washwashed with water
  3. customdecomposed with 100 ml of 30% strength sodium hydroxide solution at 10-15° C
  4. customThe oil formed
  5. extractionwas extracted
  6. stirringby shaking with ethyl acetate
  7. washwashed with water
  8. dry with materialthe organic phase was dried with sodium sulfate
  9. customThe product was then precipitated with isopropanolic HCl
  10. filtrationfiltered off with suction
  11. customdried in vacuo

Sources & evidence

ORD record
ord-5facb5f62df24784972b9e1daea401d9
Source dataset
uspto-grants-2002_04
Patent number
US06369088B2

Reaction notes

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