Phosphoric Acid → HCID 11379407, compound

HRID 1392200Notes

Reaction equation

HRID 1392200 reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.OP(O)(O)=O.[C:20]([C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1)(=O)[CH2:21][CH3:22].[NH:30]([C:32]1C=[CH:39][C:35]([C:36]([OH:38])=[O:37])=[CH:34][CH:33]=1)N>O>[N:27]1[CH:28]=[CH:29][C:24]([C:20]2[NH:30][C:32]3[C:22]([CH:21]=2)=[CH:39][C:35]([C:36]([OH:38])=[O:37])=[CH:34][CH:33]=3)=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 1004Phosphoric AcidHCID 120894-Hydrazinobenzoic acidHCID 14812Phosphorus oxide (P4O10)HCID 743431-(4-Pyridinyl)-1-propanone

Product 1

HCID 11379407HCID 11379407, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

20 g of P2O5 were admixed with 12.5 ml of H3PO4 (85%), resulting in a strong increase of the temperature of the reaction mixture. The reaction mixture was then cooled to 60° C., and 8.90 g (65.84 mmol) of 4-propionylpyridine and 4.20 g (27.60 mmol) of 4-hydrazinobenzoic acid were added. The mixture was then stirred at 145° C. for 45 min. The reaction mixture was poured into water, resulting in the precipitation of the yellow product 2-pyridin-4-yl-1H-indole-5-carboxylic acid. This precipitate was filtered off with suction and washed with water until neutral. The 2-pyridin-4-yl-1H-indole-5-carboxylicacid, which was obtained by this method in quantitative yield, was used without further purification for coupling with amino acid derivatives.

Workup

  1. customresulting in
  2. temperaturea strong increase of the temperature of the reaction mixture

Sources & evidence

ORD record
ord-25eb5a77cb0c42aa872d44e987317085
Source dataset
uspto-grants-2008_03
Patent number
US07342029B2

Reaction notes

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