Sodium Hydroxide → HCID 57417107, compound

HRID 1517649Notes

Reaction equation

HRID 1517649 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([Cl:11])[CH:5]=1.[N:13]([O-])=O.[Na+].[Sn](Cl)Cl.[OH-].[Na+]>Cl.O>[Cl:11][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1[NH:10][NH2:13])[C:3]([O:2][CH3:1])=[O:12]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 1515284Methyl 4-Amino-3-chlorobenzoateHCID 23668193Sodium Nitrite

Product 1

HCID 57417107HCID 57417107, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
-10 °C

Procedure

3.0 g (16.0 mmol) methyl-4-amino-3-chlorobenzoate are suspended in 15 ml of conc. hydrochloric acid and cooled to −10° C. First a solution of 1.1 g (16.0 mmol) sodium nitrite in 15 ml of water is added dropwise, then a solution of 16.1 g (71.0 mmol) tin(II)-chloride in 13.5 ml hydrochloric acid. A precipitate settles out. The reaction mixture is made basic with 3 molar sodium hydroxide solution, then suction filtered. The precipitate is extracted with dichloromethane and water, the organic phase is dried, combined with activated charcoal and evaporated to dryness. The residue is purified by chromatography. Yield: 1.4 g (M.p.: 120° C.)

Workup

  1. filtrationsuction filtered
  2. extractionThe precipitate is extracted with dichloromethane and water
  3. customthe organic phase is dried
  4. customevaporated to dryness
  5. customThe residue is purified by chromatography

Sources & evidence

ORD record
ord-e28b0c9359424ed7b879a8902480f23e
Source dataset
uspto-grants-2012_07
Patent number
US08232286B2

Reaction notes

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