Hydroxylamine → 5-(5-Hydroxymethyl-2-pyridin-4-yl-furan-3-yl)indan-1-one oxime

HRID 271538Notes

Reaction equation

HRID 271538 reaction equation
[OH:1][CH2:2][C:3]1[O:7][C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[C:5]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[C:19](=O)[CH2:18][CH2:17]3)[CH:4]=1.[NH2:24][OH:25]>C(O)C>[OH:1][CH2:2][C:3]1[O:7][C:6]([C:8]2[CH:9]=[CH:10][N:11]=[CH:12][CH:13]=2)=[C:5]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[C:19](=[N:24][OH:25])[CH2:18][CH2:17]3)[CH:4]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 693172355-(5-Hydroxymethyl-2-pyridin-4-yl-furan-3-yl)indan-1-one

Product 1

HCID 1363552565-(5-Hydroxymethyl-2-pyridin-4-yl-furan-3-yl)indan-1-one oximeYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product of Step 3 (150 mg, (0.49 mmol) was heated at reflux in ethanol (10 ml) containing 50% aqueous hydroxylamine (1 ml) for 2 hours. The solution was concentrated in vacuo to an oil and purified by silica gel chromatography eluting with 1:9:90.880 ammonia:ethanol:dichloromethane to afford the title product (128 mg, 81%); MS(ES+) m/e 321 [M+H]+.

Workup

  1. concentrationThe solution was concentrated in vacuo to an oil
  2. custompurified by silica gel chromatography
  3. washeluting with 1:9:90.880 ammonia

Sources & evidence

ORD record
ord-57579b5a9cd24b56ae4b66d5f540c816
Source dataset
uspto-grants-2008_11
Patent number
US07452906B2

Reaction notes

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