Hydroxyamine hydrochloride → HCID 178462460, compound

HRID 2215668Notes

Reaction equation

HRID 2215668 reaction equation
[CH2:1]([N:3]1[C:12]2[CH:11]=[CH:10][C:9]([CH:13]([CH3:15])[CH3:14])=[CH:8][C:7]=2[C:6](=[O:16])[C:5]2[C:17](=O)[C:18]3[C:23]([C:4]1=2)=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH3:2].Cl.[NH2:26][OH:27]>C(N(CC)CC)C.C(O)C>[CH2:1]([N:3]1[C:12]2[CH:11]=[CH:10][C:9]([CH:13]([CH3:15])[CH3:14])=[CH:8][C:7]=2[C:6](=[O:16])[C:5]2[C:17](=[N:26][OH:27])[C:18]3[C:23]([C:4]1=2)=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH3:2]

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 21952567HCID 21952567, compound

Product 1

HCID 178462460HCID 178462460, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8471TriethylamineSolvent

Procedure

5-Ethyl-8-isopropyl-5,10-dihydro-11H-indeno[1,2-b]quinolin-10,11-dione (300 mg, 0.95 mmol) was dissolved in a solution of hydroxylamine hydrochloride (525 mg, 7.6 mmol) and triethylamine (0.5 mL) in 20 mL of ethanol. The solution was refluxed overnight and then concentrated dryness. The residue was diluted with water and extracted with chloroform twice. The combined organic layers were washed with saturated sodium chloride solution, dried with sodium sulfate followed by evaporation to remove the solvent. The title compound was obtained by subjecting the resulting residue to silica gel-chromatography (chloroform:actone=20:1) and then to crystallization from diethyl ether. 1H-NMR (CDCl3) δ 1.32 (6H, d, CH(CH3)2, 1.73 (3H, t, NCH2CH3), 3.03 (1H, septet, CH), 4.79 (2H, q, NCH2), 7.41-8.00 (6H, m, Ar—H), 8.25 (1H, s, H-9), 15.31 (1H, s, N═OH)

Workup

  1. temperatureThe solution was refluxed overnight
  2. concentrationconcentrated dryness
  3. additionThe residue was diluted with water
  4. extractionextracted with chloroform twice
  5. washThe combined organic layers were washed with saturated sodium chloride solution
  6. dry with materialdried with sodium sulfate
  7. customfollowed by evaporation
  8. customto remove the solvent

Sources & evidence

ORD record
ord-39379e87892b40b9a829c380b66c65a0
Source dataset
uspto-grants-2006_09
Patent number
US07109338B2

Reaction notes

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