Hydrochloric Acid → HCID 178426272, compound

HRID 478839Notes

Reaction equation

HRID 478839 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[OH:11].Cl.[N:13]([O-])=O.[Na+].[CH3:17][C:18]1[NH:19][N:20]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)[C:21](=[O:23])[CH:22]=1.C(=O)([O-])O.[Na+]>O.C(O)C>[OH:11][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:2]=1[N:1]=[N:13][C:22]1[C:18]([CH3:17])=[N:19][N:20]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)[C:21]=1[OH:23])[C:6]([OH:8])=[O:7]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 1375664-Amino-3-hydroxybenzoic acidHCID 516892Sodium BicarbonateHCID 27368983-Methyl-1-(4-methylphenyl)-1H-pyrazol-5-olHCID 23668193Sodium Nitrite

Product 1

HCID 178426272HCID 178426272, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4-amino-3-hydroxybenzoic acid (0.77 g, 0.005 mol.) in 1N aqu. hydrochloric acid (15.0 mL) was cooled to 0° C. and treated slowly with a solution of sodium nitrite (0.38 g; 0.0055 mol.) in water (5.0 mL). After addition the solution was stirred at 0° C. for 10 min. then 3-methyl-1-(4-methylphenyl)-3-pyrazolin-5-one (0.94 g; 0.005 mol.) was added in one portion. Ethanol (15.0 mL) was added followed by sat. aqu. sodium hydrogen carbonate until the pH of the solution was 8 (ca. 10 mL needed). The red solution was then stirred at room temperature for 16 h.

Workup

  1. additionAfter addition the solution
  2. stirringThe red solution was then stirred at room temperature for 16 h.

Sources & evidence

ORD record
ord-93369d921641435a96f81c582a9a3a8d
Source dataset
uspto-grants-2003_11
Patent number
US06642265B1

Reaction notes

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