Isopropanol → HCID 136351080, compound

HRID 536427Notes

Reaction equation

HRID 536427 reaction equation
COC([C:5]1[C:10]2[N:11]([CH3:14])[N:12]=[N:13][C:9]=2[C:8]([CH:15]=O)=[CH:7][CH:6]=1)=O.Cl.[NH2:18][OH:19].[C:20]([O-:23])(=O)C.[Na+].[CH:25]([OH:28])(C)C>O>[CH3:14][N:11]1[C:10]2[CH:5]=[C:6]([C:20]([O:28][CH3:25])=[O:23])[CH:7]=[C:8]([CH:15]=[N:18][OH:19])[C:9]=2[N:13]=[N:12]1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 58524125HCID 58524125, compound

Product 1

HCID 136351080HCID 136351080, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4-formyl-1-methylbenzotriazole-7-carboxylic acid methyl ester (0.15 g) in isopropyl alcohol (10 ml) and water (5 ml) was treated with hydroxylamine hydrochloride (0.05 g) and sodium acetate (0.06 g) and stirred for 2 h. Isopropyl alcohol was removed and the remaining mixture was extracted with ethyl acetate (3×5 ml). The combined organic layers were dried over sodium sulfate and concentrated to give 1-methyl-6-methoxycarbonylbenzotriazole-4-carbaldehyde oxime (0.14 g). 1H-NMR (400 MHz, DMSO): 12.06 (s, 1H), 8.55 (s, 1H), 8.11 (d, 1H), 7.79 (d, 1H), 4.57 (s, 3H), 3.93 (s, 3H). LC-MS: m/z=235.08 (M+H).

Workup

  1. customIsopropyl alcohol was removed
  2. extractionthe remaining mixture was extracted with ethyl acetate (3×5 ml)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e133436f52934a41bd1e6b7a4a3d924b
Source dataset
uspto-grants-2014_10
Patent number
US08859592B2

Reaction notes

Loading…