Hydrochloric Acid → HCID 89647544, compound

HRID 2274585Notes

Reaction equation

HRID 2274585 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[ClH:14].[N:15]([O-])=O.[Na+]>O>[ClH:14].[NH:1]([C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])[NH2:15]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 120322-Amino-5-nitrobenzoic acidHCID 23668193Sodium Nitrite

Product 1

HCID 89647544HCID 89647544, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To an ice cooled solution of 2-amino-5-nitrobenzoic acid (50.0 g, 274.5 mmol) in water (350 mL) was added conc. HCl (404 mL). The reaction mixture was stirred until the salt had precipitated out. A solution of sodium nitrite (29.0 g, 411.8 mmol) in water (300 mL) was slowly added at 0° C. with stirring for 15 min. This reaction mixture was slowly added to ice-cold sulfurous acid (2.5 L) followed by stirring at RT for 12 h. The reaction mixture was again cooled to 0° C. and conc. HCl was added unitl solid separates out. The solid was filtered, washed with cold HCl and vacuum dried to afford the title compound as a yellow colored solid 60 g (93%), which was used without further purification. Rf=0.10 (10% MeOH in DCM).

Workup

  1. customhad precipitated out
  2. stirringwith stirring for 15 min
  3. stirringby stirring at RT for 12 h
  4. filtrationThe solid was filtered
  5. washwashed with cold HCl and vacuum
  6. customdried

Sources & evidence

ORD record
ord-3912e6796f4c4a8a8111462ed53d1316
Source dataset
uspto-grants-2015_09
Patent number
US09126979B2

Reaction notes

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