Hydrochloric Acid → HCID 22494951, compound

HRID 1862594Notes

Reaction equation

HRID 1862594 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([N+:13]([O-:15])=[O:14])[CH:4]=1)#[N:2].CO.[ClH:18]>C1COCC1>[Cl-:18].[N+:13]([C:5]1[CH:4]=[C:3]([CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])[CH2:1][NH3+:2])([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 11356202Methyl 4-cyano-2-nitrobenzoate

Product 1

HCID 22494951HCID 22494951, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

700 ml of a 1 M BH3 solution in THF (0.7 mol) are metered in the course of one hour at 40-50° C. into a solution of 144 g (0.7 mol) of methyl 4-cyano-2-nitrobenzoate in 250 ml of THF and the mixture is subsequently refluxed for a further 1.5 hours. The reaction mixture is then treated with 600 ml of methanol saturated with hydrogen chloride gas, with ice-cooling, and refluxed for one hour. The mixture is concentrated completely under atmospheric pressure and reevaporated with 700 ml of methanol. The residue which remains is stirred with 500 ml of ethyl acetate and filtered, and the product is dried. This gives 115 g (67%) of 3-nitro-4-methoxycarbonylbenzyl-ammonium chloride of melting point 247-248° C.

Workup

  1. temperaturethe mixture is subsequently refluxed for a further 1.5 hours
  2. temperaturecooling
  3. temperaturerefluxed for one hour
  4. concentrationThe mixture is concentrated completely under atmospheric pressure
  5. customreevaporated with 700 ml of methanol
  6. filtrationfiltered
  7. customthe product is dried

Sources & evidence

ORD record
ord-8afbc4dec7ff4ba1aad4e756a0be980f
Source dataset
uspto-grants-2003_03
Patent number
US06538150B2

Reaction notes

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