Ammonia → HCID 19992378, compound

HRID 345429Notes

Reaction equation

HRID 345429 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[OH:12])[NH:8][C:7](=[O:13])[C:6]2([CH3:15])[CH3:14].[N:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23](O)=O)=[CH:18][CH:17]=1.N>>[N:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]2[O:12][C:11]3[CH:10]=[C:9]4[NH:8][C:7](=[O:13])[C:6]([CH3:15])([CH3:14])[C:5]4=[CH:4][C:3]=3[N:2]=2)=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 342284-Pyridineacetic acidHCID 19992358HCID 19992358, compound

Product 1

HCID 19992378HCID 19992378, compound

Procedure

4.52 g. 5-Amino-1,3-dihydro-3,3-dimethyl-6-hydroxy-2H-indol-2-one hydrochloride and 3.65 g. 4-pyridylacetic acid were heated in 20 g. polyphosphoric acid for 30 minutes to 170° C. and the reaction mixture subsequently poured on to ice. A concentrated aqueous solution of ammonia was added thereto to give a pH of 10, the precipitate obtained was filtered off with suction, successively washed with water, methanol and diethyl ether and then dried to constant weight to give 3.20 g. (55% of theory) of the title compound; m.p. 208°-211° C.

Workup

  1. customto give a pH of 10
  2. customthe precipitate obtained
  3. filtrationwas filtered off with suction
  4. washsuccessively washed with water, methanol and diethyl ether
  5. customdried to constant weight
  6. customto give 3.20 g

Sources & evidence

ORD record
ord-74a07ec237f742c6b336860ce876b8ec
Source dataset
uspto-grants-1991_10
Patent number
US05057526

Reaction notes

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