Hydrochloric Acid → HCID 15125649, compound

HRID 2107792Notes

Reaction equation

HRID 2107792 reaction equation
[Na].[N+:2]([C:5]1[C:14]([NH:15]C(=O)C)=[C:13]([Cl:19])[CH:12]=[C:7]([C:8]([O:10][CH3:11])=[O:9])[C:6]=1[OH:20])([O-:4])=[O:3].Cl>CO>[N+:2]([C:5]1[C:14]([NH2:15])=[C:13]([Cl:19])[CH:12]=[C:7]([C:8]([O:10][CH3:11])=[O:9])[C:6]=1[OH:20])([O-:4])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5360545SodiumHCID 15125648HCID 15125648, compound

Product 1

HCID 15125649HCID 15125649, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

Sodium (3.8 g, 0.17 m) is dissolved in 150 ml methanol and to this is added methyl 3-nitro-4-acetylamino-5-chlorosalicylate (5 g, 17 mmol) under nitrogen. This mixture is then heated to reflux overnight. The mixture is then cooled to 20° C. and poured into a rapidly stirring mixture of ice and 10% HCl (650 ml). The ppt. which forms is filtered, washed with H2O and dried to obtain methyl 3-nitro-4-amino-5-chlorosalicylate as a yellow powder which is used directly in the next step.

Workup

  1. temperatureThis mixture is then heated
  2. temperatureto reflux overnight
  3. additionpoured into
  4. filtrationwhich forms is filtered
  5. washwashed with H2O
  6. customdried

Sources & evidence

ORD record
ord-0ca95643227f4ce29efb1077c03d105d
Source dataset
uspto-grants-1990_06
Patent number
US04935511

Reaction notes

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