Hydroxyamine hydrochloride → HCID 136025149, compound

HRID 1381506Notes

Reaction equation

HRID 1381506 reaction equation
Cl.[NH2:2][OH:3].[CH:4]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:14](=O)[C:8]=2[CH:7]=[CH:6][N:5]=1>C(N(CC)CC)C>[OH:3][N:2]=[C:14]1[C:8]2[CH:7]=[CH:6][N:5]=[CH:4][C:9]=2[CH:10]=[CH:11][CH:12]=[CH:13]1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 13357470HCID 13357470, compound

Product 1

HCID 136025149HCID 136025149, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Hydroxylamine hydrochloride (2.20 g, 0.317 mole) was added to a stirred mixture of cyclohepta[1,2-c]pyridin5-one and triethylamine (15.00 ml) and the resulting yellow solution was stirred overnight at its reflux temperature. The pale yellow solution was cooled to room temperature, then concentrated by solvent evaporation to a pasty yellow solid. The solid was dissolved in a mixture of water and diethyl ether (1:1, ~700ml) and the yellow Et2O layer was separated and extracted with water (2X, 500 ml), washed with brine, then dried (MgSO4). Filtration through celite followed by concentration of the filtrate gave 2.30g (53%) of a yellow solid, which after trituration with hexane and recrystallization from aqueous ethanol, gave the desired product, m.p. 164°-167° C.

Workup

  1. temperaturereflux temperature
  2. concentrationconcentrated by solvent evaporation to a pasty yellow solid
  3. dissolutionThe solid was dissolved in a mixture of water and diethyl ether (1:1, ~700ml)
  4. customthe yellow Et2O layer was separated
  5. extractionextracted with water (2X, 500 ml)
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationFiltration through celite

Sources & evidence

ORD record
ord-da2c48fc9fcd421cafdb7cbb3b3ec3c5
Source dataset
uspto-grants-1989_02
Patent number
US04803210

Reaction notes

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