HCID 12953039, compound → HCID 12953013, compound

HRID 2413088Notes

Reaction equation

HRID 2413088 reaction equation
[Cl:1][C:2]1[C:9]([N+:10]([O-])=O)=[CH:8][CH:7]=[C:6]([CH3:13])[C:3]=1[C:4]#[N:5]>C(O)C.Cl.O>[Cl:1][C:2]1[C:3]([C:4]#[N:5])=[C:6]([CH3:13])[CH:7]=[CH:8][C:9]=1[NH2:10]

Participants

5

Reactant 1

HCID 12953039HCID 12953039, compound

Product 1

HCID 12953013HCID 12953013, compoundYield 31.8%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 2-chloro-6-methyl-3-nitrobenzonitrile (6.3 g) in ethanol (23 ml) was added to a solution of stannous chloride dihydrate (21.7 g) in concentrated hydrochloric acid (19 ml). The mixture was then heated at reflux for 15 minutes, cooled and diluted with water (200 ml). The fine white powder which precipitated was separated, dried and crystallized from ethanol (10 ml) to give 2-chloro-3-cyano-4-methylaniline (1.7 g), m.p. 117°-119° C., in the form of colourless crystals.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureat reflux for 15 minutes
  3. temperaturecooled
  4. customThe fine white powder which precipitated
  5. customwas separated
  6. customdried
  7. customcrystallized from ethanol (10 ml)

Sources & evidence

ORD record
ord-c5210092ee744324ac190f1af6935309
Source dataset
uspto-grants-1985_01
Patent number
US04496390

Reaction notes

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