Hydrochloric Acid → HCID 20212863, compound

HRID 1906219Notes

Reaction equation

HRID 1906219 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH2:11])=[O:10])=[CH:4][CH:3]=1.[N:12]([O-])=O.[Na+].[ClH:16]>O>[ClH:16].[NH:1]([C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([NH2:11])=[O:10])=[CH:6][CH:7]=1)[NH2:12]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 2380342-(4-Aminophenyl)acetamideHCID 23668193Sodium Nitrite

Product 1

HCID 20212863HCID 20212863, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of 2-(4-aminophenyl)acetamide (19.5 g) in concentrated hydrochloric acid (43 ml) was added an ice cold solution of sodium nitrite (9.43 g) in water (25 ml) at such a rate that the temperature of the mixture remained between -5° and +5° C. When the addition was complete the solution was stirred at 0° C. for 15 min. This was then added to a stirred solution of stannous chloride (146.3 g) in concentrated hydrochloric acid (86 ml) at -10° C. The mixture was stirred for 30 min., poured into ice cold ethanol (750 ml) and the suspension was stirred for a further 30 min. Collection of the solid by filtration and washing with ethanol followed by ether gave the title compound as a white powder (20.6 g). This material was 62% pure but was contaminated with sodium chloride. It was used in the next stage without further purification.

Workup

  1. customremained between -5° and +5° C
  2. additionWhen the addition
  3. stirringThe mixture was stirred for 30 min.
  4. stirringthe suspension was stirred for a further 30 min
  5. customCollection of the solid
  6. filtrationby filtration
  7. washwashing with ethanol

Sources & evidence

ORD record
ord-c69f7f68671c4c3db1daaab3f3d7c865
Source dataset
uspto-grants-1987_03
Patent number
US04650810

Reaction notes

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