2-Aminopyridine → 4-Hydroxy-2-methyl-N-(2-pyridyl)-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxide

HRID 1730541Notes

Reaction equation

HRID 1730541 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]=[CH:28][CH:27]=[CH:26][N:25]=1>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]=[CH:28][CH:27]=[CH:26][N:25]=1)=[O:4])=[CH:18][CH:17]=[CH:16][CH:15]=3

Participants

4

Reactant 2

HCID 104392-AminopyridineHCID 546906514-hydroxy-2-methyl-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxylic acid methylester-1,1-dioxide

Product 1

HCID 546959384-Hydroxy-2-methyl-N-(2-pyridyl)-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxide

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture consisting of 9.53 gm (0.03 mol) of 4-hydroxy-2-methyl-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxylic acid methylester-1,1-dioxide, 3.8 gm (0.04 mol) of 2-aminopyridine and 250 ml of anhydrous xylene was refluxed for 14 hours in a Soxhlet apparatus equippedwith a 4-A-molecular sieve. After cooling and standing overnight, the crystals which had formed were suction-filtered off and recrystallized from ethylene chloride, yielding 5.4 gm (42% of theory) of the crystallinecompound of the formula ##SPC14##

Workup

  1. temperaturewas refluxed for 14 hours in a Soxhlet apparatus equippedwith a 4-A-molecular sieve
  2. temperatureAfter cooling
  3. customthe crystals which had formed
  4. filtrationwere suction-filtered off
  5. customrecrystallized from ethylene chloride
  6. customyielding 5.4 gm (42% of theory) of the crystallinecompound of the formula

Sources & evidence

ORD record
ord-a5959563d086429a962596c39904ae2f
Source dataset
uspto-grants-1976_11
Patent number
US03992535

Reaction notes

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