Ammonia → 8-methoxy-3-phenyl-2,7-naphthyridin-1(2H)-one

HRID 1034937Notes

Reaction equation

HRID 1034937 reaction equation
[CH3:1][O:2][C:3]1[N:12]=[CH:11][CH:10]=[C:9]([C:13]#[C:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:4]=1[C:5](OC)=[O:6].[NH3:21]>CO>[CH3:1][O:2][C:3]1[N:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5](=[O:6])[NH:21][C:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:13]2

Participants

4

Reactant 2

HCID 222AmmoniaHCID 58093657Methyl 2-methoxy-4-(phenylethynyl)nicotinate

Product 1

HCID 580937988-methoxy-3-phenyl-2,7-naphthyridin-1(2H)-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
115 °C

Procedure

Methyl 2-methoxy-4-(phenylethynyl)nicotinate (100 mg, 0.37 mmol) is dissolved in 7% NH3 in MeOH (3 mL) and heated at 115° C. in a sealed tube for 24 hours. The reaction mixture is cooled to 0° C. and the cyclized product is crystallized out. The compound is collected by filtration and dried after washing with hexanes. MS m/z 253.1 (M+1).

Workup

  1. temperatureThe reaction mixture is cooled to 0° C.
  2. customthe cyclized product is crystallized out
  3. filtrationThe compound is collected by filtration
  4. customdried
  5. washafter washing with hexanes

Sources & evidence

ORD record
ord-29beea0dbb9042dda025b86be76c15db
Source dataset
uspto-grants-2013_10
Patent number
US08546370B2

Reaction notes

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