Hydrochloric Acid → HCID 13079849, compound

HRID 2418649Notes

Reaction equation

HRID 2418649 reaction equation
Cl.N[C:3]1[C:8]([Br:9])=[CH:7][C:6]([C:10]2[CH:11]=[C:12]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:13]([CH3:16])=[N:14][CH:15]=2)=[CH:5][C:4]=1[Br:22].N([O-])=O.[Na+].[PH2](O)=O>C(O)(=O)C.O.C(N(CC)CC)C>[Br:9][C:8]1[CH:7]=[C:6]([C:10]2[CH:11]=[C:12]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:13]([CH3:16])=[N:14][CH:15]=2)[CH:5]=[C:4]([Br:22])[CH:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 4124402Phosphinic AcidHCID 13079853HCID 13079853, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 13079849HCID 13079849, compoundYield 50.3%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent3×HCID 8471TriethylamineSolvent

Procedure

Hydrochloric acid (11.5N, 0.90 ml) was added to 5-(4-amino-3,5-dibromophenyl)-3-ethoxycarbonyl-2-methyl pyridine (2 g) in glacial acetic acid (20 ml). Sodium nitrite (0.37 g) in water (2 ml) was added at 0°-5° C. and, after standing for 0.5 hour at this temperature, the mixture was poured into 30% aqueous hypophosphorous acid (3.88 g) in water (10 ml). The mixture was stirred at room temperature for 0.5 hour, diluted with water, made alkaline with triethylamine and extracted with diethyl ether. The extract was washed with sodium bicarbonate solution and water, dried and filtered through a column of silica. Concentration of the filtrate and recrystallisation of the residue from petroleum ether (b.p. 40°-60°) gave the title compound (0.97 g), m.p. 100°-2°.

Workup

  1. extractionextracted with diethyl ether
  2. washThe extract was washed with sodium bicarbonate solution and water
  3. customdried
  4. filtrationfiltered through a column of silica
  5. customConcentration of the filtrate and recrystallisation of the residue from petroleum ether (b.p. 40°-60°)

Sources & evidence

ORD record
ord-2b2d14c96c3b4ce699d677db596d6935
Source dataset
uspto-grants-1984_09
Patent number
US04473395

Reaction notes

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