Hydrochloric Acid → HCID 178525249, compound

HRID 436209Notes

Reaction equation

HRID 436209 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:3]=1[CH:4]=[CH:5][C:6]([OH:8])=[O:7].Cl.[N:15]([O-])=O.[Na+].S([O-])([O-])=O.[Na+].[Na+]>O>[Cl:13][C:10]1[CH:9]=[C:3]2[C:2](=[CH:12][CH:11]=1)[NH:1][N:15]=[C:4]2[CH2:5][C:6]([OH:8])=[O:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24437Sodium SulfiteHCID 23668193Sodium NitriteHCID 53401601HCID 53401601, compound

Product 1

HCID 178525249HCID 178525249, compoundYield 22.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

To a suspension of 2 -amino-5-chlorocinnamic acid (3.0 g) in water (35 ml), there is added conc. hydrochloric acid (11 ml). To the resulting solution cooled with ice, a solution of sodium nitrite (1.0 g) in water (2 ml) is dropwise added while stirring, and stirring is continued for 30 minutes. Anhydrous sodium sulfite (5.0 g) is portionwise added thereto. After stirring at room temperature for 1 hour, the resulting mixture is admixed with water (100 ml) and heated on an oil bath for 0.5 to 1 hour while refluxing. The reaction mixture is filtered. The collected material is washed with hot water. The washing water is combined with the filtrate and concentrated. The residue is crystallized from hot water to give 5-chloro-1H-indazole-3-acetic acid (0.7 g) as white needles melting at 205° C (decomp.)

Workup

  1. temperatureTo the resulting solution cooled with ice
  2. stirringstirring
  3. stirringAfter stirring at room temperature for 1 hour
  4. temperatureheated on an oil bath for 0.5 to 1 hour
  5. temperaturewhile refluxing
  6. filtrationThe reaction mixture is filtered
  7. washThe collected material is washed with hot water
  8. concentrationconcentrated
  9. customThe residue is crystallized from hot water

Sources & evidence

ORD record
ord-b74cba0da1cc46608c18feef6110de61
Source dataset
uspto-grants-1977_02
Patent number
US04008070

Reaction notes

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