Hydrochloric Acid → HCID 13260283, compound

HRID 1649016Notes

Reaction equation

HRID 1649016 reaction equation
[N:1]1[C:2]([C:10]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]3[C:11]=2[CH2:12][CH2:13][C:14](=[O:22])[NH:15]3)=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.Cl.[N:24]([O-])=[O:25].[Na+]>O>[N:24]([C:3]1[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]2=[N:1][C:2]=1[C:10]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]2[C:11]=1[CH2:12][CH2:13][C:14](=[O:22])[NH:15]2)=[O:25]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 13260279HCID 13260279, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 13260283HCID 13260283, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 5-(imidazo[1,2-a]pyridine-2-yl)-8-methoxy-3,4-dihydrocarbostyril (2.5 g) in 300 ml of water was added 1.71 ml of concentrated hydrochloric acid. The mixture was heated and the solution was cooled to 50° C. and 10 ml of aqueous solution having dissolved therein 0.65 g of sodium nitrite was added dropwise to the solution at 50° C. with stirring. After completion of addition, the reaction was continued for 2 hours and the reaction mixture was allowed to stand overnight at room temperature. Crystals which precipitated were collected by filtration, and recrystallized from methanol to give 1.9 g of 5-(3-nitrosoimidazo[1,2-a]pyridine-2-yl)-8-methoxy-3,4-dihydrocarbostyril.

Workup

  1. temperatureThe mixture was heated
  2. additionAfter completion of addition
  3. waitto stand overnight at room temperature
  4. customCrystals which precipitated
  5. filtrationwere collected by filtration
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-0ba84a3b195345e481a0bb48a1ea9b53
Source dataset
uspto-grants-1983_11
Patent number
US04414390

Reaction notes

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