Acetic Acid → HCID 58641496, compound

HRID 1057500Notes

Reaction equation

HRID 1057500 reaction equation
[NH:1]1[C:6]2=[N:7][C:8]([CH:11]=O)=[CH:9][CH:10]=[C:5]2[CH2:4][CH2:3][CH2:2]1.S([O-])([O-])(=O)=O.[Na+].[Na+].[CH:20]([NH2:23])([CH3:22])[CH3:21].C(O)(=O)C>ClCCl>[CH3:21][CH:20]([NH:23][CH2:11][C:8]1[N:7]=[C:6]2[NH:1][CH2:2][CH2:3][CH2:4][C:5]2=[CH:10][CH:9]=1)[CH3:22]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6363IsopropylamineHCID 24436Sodium SulfateHCID 218737255,6,7,8-Tetrahydro-1,8-naphthyridine-2-carbaldehyde

Product 1

HCID 58641496HCID 58641496, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1,2,3,4-tetrahydropyridino[2,3-b]pyridine-7-carbaldehyde in dry dichloromethane (32 mL) were added 4° A seives, sodium sulfate and isopropyl amine. The mixture was cooled to 0° C. followed by the addition of acetic acid (300 μL). The resulting mixture was stirred at room temperature under nitrogen for 18 hrs. The mixture was filtered through celite, diluted with ethyl acetate, washed with saturated sodium bicarbonate and brine, dried over sodium sulfate, evaporated concentrated in vacuo and purified by flash chromatography(10% MeOH/CH2Cl2 ). EI-MS m/z 206 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through celite
  2. additiondiluted with ethyl acetate
  3. washwashed with saturated sodium bicarbonate and brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography(10% MeOH/CH2Cl2 )

Sources & evidence

ORD record
ord-8fcee0231b5f41dfa71e8d05a7d8ba6f
Source dataset
uspto-grants-2003_02
Patent number
US06514964B1

Reaction notes

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