Ammonia → HCID 10016371, compound

HRID 1606156Notes

Reaction equation

HRID 1606156 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH2:14][C:15]#N)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[OH-:19].[Na+].N.Cl.[OH2:23]>C(O)C>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH2:14][C:15]([OH:23])=[O:19])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 18424281HCID 18424281, compound

Product 1

HCID 10016371HCID 10016371, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 129 g. (0.52 mole) of 5-(p-chlorobenzoyl)-1-methylpyrrole-2-acetonitrile and 88 g. (1.1 moles) of 50% sodium hydroxide solution in 800 ml. of ethanol and 500 ml. of water is stirred and refluxed for about 18 hours with slow evolution of ammonia. The solution is then cooled to about 50°C. and acidified by adding 110 ml. of concentrated hydrochloric acid. The mixture is cooled and the precipitated product, 5-(p-chlorobenzoyl)-1-methylpyrrole-2-acetic acid, is filtered and recrystallized from methanol, m.p. 193°-195°C. (dec.). A second crop is obtained upon concentration of the mother liquor for a total yield of about 67% of theoretical.

Workup

  1. additionA mixture of 129 g
  2. additionby adding 110 ml
  3. temperatureThe mixture is cooled
  4. filtrationthe precipitated product, 5-(p-chlorobenzoyl)-1-methylpyrrole-2-acetic acid, is filtered
  5. customrecrystallized from methanol, m.p. 193°-195°C. (dec.)
  6. customA second crop is obtained upon concentration of the mother liquor for a total yield of about 67% of theoretical

Sources & evidence

ORD record
ord-2c3ba2e7dfd44fc1823f7eeb4e950ee1
Source dataset
uspto-grants-1976_04
Patent number
US03952012

Reaction notes

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