Hydroxyamine hydrochloride → HCID 178469477, compound

HRID 1680529Notes

Reaction equation

HRID 1680529 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[CH2:10][CH2:11][CH2:12][C:13](=O)[C:14]=2[C:15]=1[OH:16])=[O:5])[CH3:2].Cl.[NH2:19][OH:20]>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[CH2:10][CH2:11][CH2:12][C:13](=[N:19][OH:20])[C:14]=2[C:15]=1[OH:16])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 178469478HCID 178469478, compound

Product 1

HCID 178469477HCID 178469477, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 80 ml of ethyl alcohol were added 2.35 g of 4-hydroxy-5-oxo-5,6,7,8-tetrahydroquinoline-3-carboxylic acid ethyl ester and 0.69 g of hydroxylamine hydrochloride. The resulting reaction mixture was refluxed on an oil bath for 1 hour. After the ethyl alcohol was distilled off under reduced pressure, the residue was dissolved in dilute hydrochloric acid and the resulting solution was adjusted to pH 5.8 with 10% potassium carbonate. The crystals so precipitated were separated by filtration to obtain a yield of 1.8 g of the desired compound. This compound melted (and decomposed) at 245°-247° C. (uncorrected values). Its infrared absorption spectrum (KBr tablet) had absorption peaks at 3240, 3060, 2960, 2920, 1720, 1650, 1550, and 1185 cm-1, and its n.m.r. spectrum (CF3COOH, 60Mc, TMS) had signals at δ values of 1.50 (3H, t, J=7.5 Hz), 2.0-2.6 (2H, m), 3.0-3.5 (4H, m), 4.6 (2H, q, J=7.5 Hz), and 8.95 (1H, s).

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed on an oil bath for 1 hour
  3. distillationAfter the ethyl alcohol was distilled off under reduced pressure
  4. dissolutionthe residue was dissolved in dilute hydrochloric acid
  5. customThe crystals so precipitated
  6. customwere separated by filtration

Sources & evidence

ORD record
ord-92fc2a116c884e97880c5191d4e64c54
Source dataset
uspto-grants-1981_06
Patent number
US04273932

Reaction notes

Loading…