2-Amino-4-methylpyridine → HCID 13260242, compound

HRID 1649014Notes

Reaction equation

HRID 1649014 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9](=[O:17])[NH:10]2)=O.[NH2:18][C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][N:20]=1>C(#N)C>[ClH:1].[CH3:25][C:23]1[CH:22]=[CH:21][N:20]2[CH:2]=[C:3]([C:5]3[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]4[C:6]=3[CH:7]=[CH:8][C:9](=[O:17])[NH:10]4)[N:18]=[C:19]2[CH:24]=1

Participants

4

Reactant 2

HCID 15332-Amino-4-methylpyridineHCID 155904845-(Chloroacetyl)-8-methoxyquinolin-2(1H)-one

Product 1

HCID 13260242HCID 13260242, compoundYield 58.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-Chloroacetyl-8-methoxycarbostyril (5 g), 2-amino-4-picoline (6.45 g) and acetonitrile (40 ml) were reacted with refluxing for 3 hours, and the reaction mixture was cooled with ice water. Crystals which formed were collected by filtration. The crystals were suspended in acetone-methanol and the suspension was adjusted to pH of about 1 by the addition of concentrated hydrochloric acid. Crystals which formed were collected by filtration and recrystallized from methanol to give 4.0 g of 5-(7-methylimidazo[1,2-a]pyridine-2-yl)-8-methoxycarbostyril monohydrochloride 3/2 hydrate.

Workup

  1. temperaturewith refluxing for 3 hours
  2. customCrystals which formed
  3. filtrationwere collected by filtration
  4. additionthe suspension was adjusted to pH of about 1 by the addition of concentrated hydrochloric acid
  5. customCrystals which formed
  6. filtrationwere collected by filtration
  7. customrecrystallized from methanol

Sources & evidence

ORD record
ord-6c2e50dbea5b4b8f9dabc6f1b5763f13
Source dataset
uspto-grants-1983_11
Patent number
US04414390

Reaction notes

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