Methyl p-toluenesulfonate → HCID 12378150, compound

HRID 1395274Notes

Reaction equation

HRID 1395274 reaction equation
[C:1]([NH:4][C:5]1[N:14]=[C:13]2[C:8]([C:9]([CH3:15])=[CH:10][CH:11]=[N:12]2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[C:16]1([CH3:27])[CH:21]=[CH:20][C:19]([S:22]([O:25]C)(=[O:24])=[O:23])=[CH:18][CH:17]=1>C(#N)C>[C:16]1([CH3:27])[CH:17]=[CH:18][C:19]([S:22]([O-:25])(=[O:23])=[O:24])=[CH:20][CH:21]=1.[C:1]([NH:4][C:5]1[N:14]=[C:13]2[C:8]([C:9]([CH3:15])=[CH:10][CH:11]=[N+:12]2[CH3:16])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6645Methyl p-toluenesulfonateHCID 12378148HCID 12378148, compound

Product 1

HCID 12378150HCID 12378150, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

7-Acetamido-4-methyl-1,8-naphthyridine (13.3 g., 0.066 mole) was refluxed for 8 hours with 12.7 g. of methyl p-toluenesulfonate in 150 ml. of dry acetonitrile. The dark purple solution was cooled at 5° for several days; 21.8 g. (85%) of felted needles, m.p. 200°-202°, was removed. Addition of a large volume of ether to the mother liquors precipitated 2.3 g. (9%) more of the salt; m.p. 185°-190°. The 1H nmr was consistent with that expected for the desired product.

Workup

  1. temperatureThe dark purple solution was cooled at 5° for several days
  2. custom(85%) of felted needles, m.p. 200°-202°, was removed
  3. additionAddition of a large volume of ether to the mother liquors
  4. customprecipitated 2.3 g

Sources & evidence

ORD record
ord-c6c43bff97bd4345a3581ad09ecb0e8b
Source dataset
uspto-grants-1980_05
Patent number
US04202981

Reaction notes

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