Potassium Hydroxide → 6-Ethynyl-8-(3-nitrophenyl)-1,7-naphthyridine

HRID 369032Notes

Reaction equation

HRID 369032 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:8]=[C:9]2[C:14](=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=3)[N:16]=1)[N:13]=[CH:12][CH:11]=[CH:10]2)(C)C.[OH-].[K+]>CO.C1(C)C=CC=CC=1>[C:6]([C:7]1[CH:8]=[C:9]2[C:14](=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=3)[N:16]=1)[N:13]=[CH:12][CH:11]=[CH:10]2)#[CH:5]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 232846376-Trimethylsilylethynyl-8-(3-nitrophenyl)-1,7-naphthyridine

Product 1

HCID 232846336-Ethynyl-8-(3-nitrophenyl)-1,7-naphthyridine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To a solution of 6-trimethylsilylethynyl-8-(3-nitrophenyl)-1,7-naphthyridine (77 mg, 0.22 mmol) in methanol (0.5 ml) and toluene (0.5 ml) is added 1N potassium hydroxide (0.22 ml). The mixture was stirred for 2 h. The suspension is filtered and the product washed with water and ether affording the title compound. Mass M+H 276; mp 215° C. decomposition.

Workup

  1. filtrationThe suspension is filtered
  2. washthe product washed with water and ether affording the title compound

Sources & evidence

ORD record
ord-c5ee397d2fb543bab80f86cccb41b574
Source dataset
uspto-grants-2000_10
Patent number
US06136821

Reaction notes

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