Hydrochloric Acid → 3-Hydroxy-5-keto-4-phenylazo-3-cyclohexenecarboxylic acid

HRID 2398065Notes

Reaction equation

HRID 2398065 reaction equation
[Na].[OH:2][C:3]1[CH2:4][CH:5]([C:10]([OH:12])=[O:11])[CH2:6][C:7](=[O:9])[CH:8]=1.[Cl-].[C:14]1([N+:20]#[N:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.NC1C=CC=CC=1.Cl.N([O-])=O.[Na+]>O.CO>[OH:2][C:3]1[CH2:4][CH:5]([C:10]([OH:12])=[O:11])[CH2:6][C:7](=[O:9])[C:8]=1[N:21]=[N:20][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 60992Benzenediazonium chlorideHCID 5360545SodiumHCID 144923703-Hydroxy-5-oxocyclohex-3-ene-1-carboxylic acidHCID 23668193Sodium Nitrite

Product 1

HCID 1355835033-Hydroxy-5-keto-4-phenylazo-3-cyclohexenecarboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

13.8 G. of sodium were dissolved in 900 ml. of methanol. 46.8 G. of 3-hydroxy-5-keto-3-cyclohexenecarboxylic acid were added to this solution. The mixture was stirred, maintained between -4° C. and -8° C. with a cooling bath and treated over a period of 30 minutes with a phenyl diazonium chloride solution prepared from 27.9 g. of aniline, 450 ml. of water, 72 ml. of concentrated hydrochloric acid and 21.0 g. of sodium nitrite in 90 ml. of water. The mixture was stirred at -5° C. to -10° C. for an additional hour. The resulting red precipitate was removed by filtration under vacuum and washed with about 1000 ml. of water, thereby there was obtained 3-hydroxy-5-keto-4-phenylazo-3-cyclohexenecarboxylic acid of melting point 218° C.

Workup

  1. temperaturemaintained between -4° C. and -8° C. with a cooling bath
  2. customprepared from 27.9 g
  3. stirringThe mixture was stirred at -5° C. to -10° C. for an additional hour
  4. customThe resulting red precipitate was removed by filtration under vacuum
  5. washwashed with about 1000 ml

Sources & evidence

ORD record
ord-aa1a8bc1a6724130869ce695fc14a3c4
Source dataset
uspto-grants-1977_05
Patent number
US04024145

Reaction notes

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