Hydrochloric Acid → HCID 21508043, compound

HRID 1287393Notes

Reaction equation

HRID 1287393 reaction equation
Cl.[Cl:2][C:3]1[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[CH:7][C:4]=1[C:5]#[N:6].[Sn].Cl.[H][H]>>[ClH:2].[NH2:11][C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[C:3]([Cl:2])[CH:10]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 5352426Tin atom2×HCID 21508222HCID 21508222, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21508043HCID 21508043, compound

Procedure

A suspension of 25 g. 2-chloro-4-nitrobenzonitrile hydrochloride and 3 g. granular tin in 147 ml. concentrated hydrochloric acid was warmed to 50°C. and when vigorous hydrogen evolution started 56 g. tin was added in 3 to 5 g. portions with cooling to maintain reaction at 90 to 100°C. The mixture was heated at reflux for 45 minutes, the unreacted tin was separated by decantation, and the resulting solution was concentrated under reduced pressure till about 80 ml. of water was collected, the residual solution was made strongly alkaline with 130 ml. 35% sodium hydroxide solution, and the solids were collected by filtration, dissolved in ether and treated with ethereal hydrogen chloride to give, on filtration, 4-amino-2-chlorobenzonitrile hydrochloride; m.p. 170°-180°C.

Workup

  1. additionA suspension of 25 g
  2. temperatureportions with cooling
  3. temperatureto maintain
  4. customreaction at 90 to 100°C
  5. temperatureThe mixture was heated
  6. temperatureat reflux for 45 minutes
  7. customthe unreacted tin was separated by decantation
  8. concentrationthe resulting solution was concentrated under reduced pressure till about 80 ml
  9. customof water was collected
  10. filtration35% sodium hydroxide solution, and the solids were collected by filtration
  11. dissolutiondissolved in ether
  12. additiontreated with ethereal hydrogen chloride

Sources & evidence

ORD record
ord-4829afdc5c6e4d76a4bdf79f3e1d18ae
Source dataset
uspto-grants-1976_10
Patent number
US03984467

Reaction notes

Loading…