Pyridine → [1,8-Diethyl-4-hydroxyimino-1,3,4,9-tetrahydro-pyrano[3.4-b]indol-1-yl]-acetic acid methyl ester

HRID 1955722Notes

Reaction equation

HRID 1955722 reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1([CH2:21][CH3:22])[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[C:8](=O)[CH2:7][O:6]1)=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:18][CH3:19].Cl.[NH2:25][OH:26].N1C=CC=CC=1>O>[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1([CH2:21][CH3:22])[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[C:8](=[N:25][OH:26])[CH2:7][O:6]1)=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 11120627Methyl (1,8-diethyl-4-oxo-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetate

Product 1

HCID 136365314[1,8-Diethyl-4-hydroxyimino-1,3,4,9-tetrahydro-pyrano[3.4-b]indol-1-yl]-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The ester of Example 4, Step B (0.5 g, 1.6 mmol), hydroxylamine hydrochloride (0.17 g, 2.4 mmol), and 25 ml pyridine were refluxed for 3.5 h. The reaction mixture was poured into water, extracted with CHCl3. The organic phase was then washed with 1.0N HCl, water, dilute NaHCO3, water, and brine, dried (MgSO4) and evaporated to yield a crude solid which was purified by filtration through a pad of silica gel and celite. The product, 0.33 g was isolated as a solid, m. p. 188°-190° C.

Workup

  1. extractionextracted with CHCl3
  2. washThe organic phase was then washed with 1.0N HCl, water, dilute NaHCO3, water, and brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto yield a crude solid which
  6. filtrationwas purified by filtration through a pad of silica gel and celite
  7. customThe product, 0.33 g was isolated as a solid, m. p. 188°-190° C.

Sources & evidence

ORD record
ord-a839befd06d946fab35884984b4e1eea
Source dataset
uspto-grants-1998_07
Patent number
US05776967

Reaction notes

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