Hydrochloric Acid → HCID 12823310, compound

HRID 544580Notes

Reaction equation

HRID 544580 reaction equation
[N:1]([O-])=O.[Na+].[NH2:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([OH:11])=[O:10].[ClH:15]>O>[Cl-:15].[C:9]([C:8]1[CH:7]=[C:6]([N+:5]#[N:1])[CH:14]=[CH:13][CH:12]=1)([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 74193-Aminobenzoic AcidHCID 23668193Sodium Nitrite

Product 1

HCID 12823310HCID 12823310, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Nitromethane (61 g.) was added to a warm (45°-50°) solution of NaOH (61 g.) in water (122 ml.) at such a rate that the temperature was maintained. At the end of the addition the temperature was raised to 55° for 10 minutes and then allowed to fall back to 50°. The mixture was chilled and neutralised to pH 7 with concentrated hydrochloric acid at ≤10°. The precipitated product was redissolved by the addition of aqueous NaOH (12.5 N; 40 ml.) to give a solution of the sodium salt of methazonic acid. A solution of NaNO2 (36.2 g.) in water (300 ml.) was added during approximately 30 minutes to a suspension of 3-aminobenzoic acid (68.6 g.) in concentrated hydrochloric acid (126.3 ml.) and water (200 ml.) at 0°-5°. The mixture was filtered to give a solution of 3-carboxybenzenediazonium chloride.

Workup

  1. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-407bc8aa6cc74618a62096c5658bc3c7
Source dataset
uspto-grants-1984_05
Patent number
US04451463

Reaction notes

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