Hydrochloric Acid → HCID 178429213, compound

HRID 1088933Notes

Reaction equation

HRID 1088933 reaction equation
Cl.[C:2](Cl)(=[O:9])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[NH2:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][C:20]=1[NH2:21])[NH:17][C:16](=[O:22])[C:15]2([CH3:24])[CH3:23].C(N(CC)CC)C.Cl>C(O)C.C(Cl)Cl>[OH2:9].[OH2:22].[OH2:9].[OH2:9].[CH3:23][C:15]1([CH3:24])[C:14]2[C:18](=[CH:19][C:20]3[NH:21][C:2]([C:3]4[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=4)=[N:11][C:12]=3[CH:13]=2)[NH:17][C:16]1=[O:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 12262826Isonicotinoyl chloride hydrochlorideHCID 135892372H-Indol-2-one, 5,6-diamino-1,3-dihydro-3,3-dimethyl-

Product 1

HCID 178429213HCID 178429213, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

3 g. (0.017 mol) Isonicotinic acid chloride hydrochloride are added portionwise to a solution of 2.9 g. (0.015 mol) 5,6-diamino-3,3-dimethylindolin-2-one in 30 ml. methylene chloride containing 4.4 ml. (0.032 mol) triethylamine and the reaction mixture is left to stir overnight. It is then evaporated to dryness in a vacuum, the residue is stirred up several times with water, filtered off with suction and the crystals obtained are heated under reflux for about 12 hours in a solution of 100 ml. ethanol containing 10 ml. concentrated hydrochloric acid. The mixture obtained is evaporated to dryness in a vacuum, the residue is stirred up with 20 ml. water and then rendered neutral with an aqueous solution of ammonia. The product is subsequently filtered off with suction, washed with water, dried and recrystallised from water containing 30% ethanol. The yield is 1.9 g. (36% of theory); m.p. 215° C.

Workup

  1. customIt is then evaporated to dryness in a vacuum
  2. stirringthe residue is stirred up several times with water
  3. filtrationfiltered off with suction
  4. customthe crystals obtained
  5. temperatureare heated
  6. temperatureunder reflux for about 12 hours in a solution of 100 ml
  7. customThe mixture obtained
  8. customis evaporated to dryness in a vacuum
  9. stirringthe residue is stirred up with 20 ml
  10. filtrationThe product is subsequently filtered off with suction
  11. washwashed with water
  12. customdried
  13. customrecrystallised from water containing 30% ethanol

Sources & evidence

ORD record
ord-26dcf72c8b4b415087a61996f9925501
Source dataset
uspto-grants-1990_10
Patent number
US04963686

Reaction notes

Loading…