Benzyloxyamine hydrochloride → HCID 19026180, compound

HRID 1821094Notes

Reaction equation

HRID 1821094 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:15](=O)[CH2:14][CH2:13][CH2:12][C:11]=2[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH2:21]([O:28][NH2:29])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>N1C=CC=CC=1>[CH2:21]([O:28][NH:29][CH:15]1[CH2:14][CH2:13][CH2:12][C:11]2[N:10]=[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:18]=[CH:17][C:16]1=2)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 102312Benzyloxyamine hydrochlorideHCID 104449777,8-Dihydro-2-(phenylmethoxy)-5(6H)-quinolinone

Product 1

HCID 19026180HCID 19026180, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To the mixture of 2-benzyloxy-7,8-dihydro-6H-quinolin-5-one (37.8 g, 149 mmoL) in pyridine (300 mL) was added O-benzylhydroxylamine hydrochloride (26.2 g, 164 mmoL) and the resulting mixture was stirred at room temperature for 24 h. The reaction was concentrated, diluted with methylene chloride and washed with saturated sodium bicarbonate (×2) and brine (×2). The methylene chloride layer was dried, filtered and concentrated. Purification by column chromatography on silica gel with 5% ethyl acetate in hexane provided the desired product (51.0 g, 96%) as an offwhite solid.

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with methylene chloride
  3. washwashed with saturated sodium bicarbonate (×2) and brine (×2)
  4. dry with materialThe methylene chloride layer was dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by column chromatography on silica gel with 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-e75e3b70f17a45d6bf760a91ebef6a63
Source dataset
uspto-grants-2009_10
Patent number
US07605265B2

Reaction notes

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