Hydroxyamine hydrochloride → 1-Methyl-5-[(3-methylpyridin-2-yl)carbohydroximoyl]tetrazole

HRID 1091996Notes

Reaction equation

HRID 1091996 reaction equation
[CH3:1][C:2]1[C:3]([C:8]([C:10]2[N:14]([CH3:15])[N:13]=[N:12][N:11]=2)=O)=[N:4][CH:5]=[CH:6][CH:7]=1.Cl.[NH2:17][OH:18]>N1C=CC=CC=1>[CH3:15][N:14]1[C:10]([C:8]([C:3]2[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][N:4]=2)=[N:17][OH:18])=[N:11][N:12]=[N:13]1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 577923253-Methylpyridin-2-yl(1-methyltetrazol-5-yl)methanone

Product 1

HCID 1363879931-Methyl-5-[(3-methylpyridin-2-yl)carbohydroximoyl]tetrazoleYield 88.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of (3-methylpyridin-2-yl(1-methyltetrazol-5-yl)methanone (2.8 g, 13.8 mmol) and hydroxylamine hydrochloride (2.4 g, 34.4 mmol) in pyridine (30 ml) is stirred three hours at 50° C. and overnight at room temperature. The solvent is evaporated and water is added to the crude mixture. The resulting suspension is filtered. The solid is washed with water and dried to give 2.65 g of 1-methyl-5-[(3-methylpyridin-2-yl)carbohydroximoyl]tetrazole [yield 88.1%; 1H-NMR (DMSO-d6) δppm: 2.6 (s, 3H), 4.02 (s, 3H), 7.35 (dd, 1H), 7.82 (d, 1H), 8.34 (d, 1H), 13.1 (s, 1H)].

Workup

  1. customThe solvent is evaporated
  2. additionwater is added to the crude mixture
  3. filtrationThe resulting suspension is filtered
  4. washThe solid is washed with water
  5. customdried

Sources & evidence

ORD record
ord-527c21828ebb41368ceba7df878d94b9
Source dataset
uspto-grants-2012_03
Patent number
US08129415B2

Reaction notes

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