2-Amino-4-methylpyridine → UH-A 46 XX

HRID 1730542Notes

Reaction equation

HRID 1730542 reaction equation
CO[C:3]([C:5]1[N:6]([CH3:22])[S:7](=[O:21])(=[O:20])[C:8]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][C:9]=2[C:10]=1[OH:11])=[O:4].[NH2:23][C:24]1[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][N:25]=1.C(OCC)(=O)C>C1(C)C(C)=CC=CC=1>[OH:11][C:10]1[C:9]2[CH:12]=[CH:13][C:14]3[C:19]([C:8]=2[S:7](=[O:20])(=[O:21])[N:6]([CH3:22])[C:5]=1[C:3]([NH:23][C:24]1[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][N:25]=1)=[O:4])=[CH:18][CH:17]=[CH:16][CH:15]=3

Participants

5

Reactant 3

HCID 15332-Amino-4-methylpyridineHCID 8857Ethyl AcetateHCID 546906514-hydroxy-2-methyl-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxylic acid methylester-1,1-dioxide

Product 1

HCID 54692988UH-A 46 XXYield 58%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

5.0 gm (0.016 mol) of 4-hydroxy-2-methyl-2H-naphtho[ 2,1-e]-1,2-thiazine-3-carboxylic acid methyl ester-1,1-dioxide were reacted with 2.2 gm (0.02 mol) of 2-amino-4-methylpyridine in 220 ml of xylene analogous to Example 10, and yielded 3.5 gm (58% of theory) of 4-hydroxy-2-methyl-N-(4-methyl-2-pyridyl)-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxide, m.p. 221° C (decomp.; from ethyl acetate).

Sources & evidence

ORD record
ord-d7a76d0387ed4a24ada61495e1e17e10
Source dataset
uspto-grants-1976_11
Patent number
US03992535

Reaction notes

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