Hydrochloric Acid → 4-chloro-N1-phenylbenzene-1,2-diamine

HRID 375594Notes

Reaction equation

HRID 375594 reaction equation
C(=O)([O-])[O-].[K+].[K+].S(S([O-])=O)([O-])=O.[Na+].[Na+].[CH:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=2[N+:29]([O-])=O)=[CH:17][CH:16]=1.Cl.[OH-].[Na+]>C(O)C.O>[CH:15]1[CH:16]=[CH:17][C:18]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=2[NH2:29])=[CH:19][CH:20]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 24489Sodium DithioniteHCID 855114-chloro-2-nitro-N-phenylaniline

Product 1

HCID 2649994-chloro-N1-phenylbenzene-1,2-diamineYield 74.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Potassium carbonate (13 g) and sodium hydrosulphite (11.4 g) were added portionwise over 3 hour to a suspension of 4-chloro-2-nitrodiphenylamine (3.6 g) in 95% ethanol (100 ml) and water (100 ml). The mixture was stirred at 23° for 20 h. The reaction mixture was then acidified to pH=4 with conc. hydrochloric acid (20 ml); then 10% solution of sodium hydroxide (80 ml) was added until pH=10 and the solution extracted with ethyl acetate (2×150 ml). The combined organic extracts were washed with brine (2×150 ml), dried and concentrated in vacuo to give the crude compound as a yellow solid (7.8 g) which was purified by flash chromatography (eluting with CH-EA 90:10 then 70:30) to give the title compound as a yellow foam (2.37 g). T.l.c. CH-EA (1:1), Rf 0.66.

Workup

  1. extractionthe solution extracted with ethyl acetate (2×150 ml)
  2. washThe combined organic extracts were washed with brine (2×150 ml)
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customto give the crude compound as a yellow solid (7.8 g) which
  6. customwas purified by flash chromatography (
  7. washeluting

Sources & evidence

ORD record
ord-8b8098602f8e43bc994ba3f6104ceecd
Source dataset
uspto-grants-1996_01
Patent number
US05486514

Reaction notes

Loading…