Ammonia → HCID 178517686, compound

HRID 1480832Notes

Reaction equation

HRID 1480832 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:16](/[CH:19]=[CH:20]/OCC)=[CH:17][N:18]=1)[C:12](OC)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1C=CC(S(O)(=O)=O)=CC=1.O.[NH3:36]>>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16]([CH:19]=[CH:20][N:36]=[C:12]2[OH:13])=[CH:17][N:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 521998p-Toluenesulfonic acid monohydrateHCID 89996003HCID 89996003, compound

Product 1

HCID 178517686HCID 178517686, compoundYield 97%

Conditions

Temperature
80 °C

Procedure

(E)-methyl 2-(benzyloxy)-5-(2-ethoxyvinyl)isonicotinate (Preparation 85, 1.2 g, 3.83 mmol) was dissolved in methanolic ammonia (7M, 28 mL) in 3 microwave tubes. The reaction mixture was sealed and heated to 80° C. for 3 days. The reaction mixture was concentrated in vacuo. The residue was dissolved in toluene (30 mL) and pTsOH.H2O (150 mg, 0.789 mmol) was added. The reaction mixture was heated at 90° C. for 2 hours. The reaction mixture was filtered and dried under vacuum, to give the title compound (937 mg, 97%).

Workup

  1. customThe reaction mixture was sealed
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionThe residue was dissolved in toluene (30 mL)
  4. temperatureThe reaction mixture was heated at 90° C. for 2 hours
  5. filtrationThe reaction mixture was filtered
  6. customdried under vacuum

Sources & evidence

ORD record
ord-6bd9ddb382634eafa61904013899a8ec
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

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