N-bromobutanimide → HCID 178432655, compound

HRID 920680Notes

Reaction equation

HRID 920680 reaction equation
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][NH:11][C:10]=1[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:17]N1C(=O)CCC1=O>C(#N)C>[CH2:1]([O:8][C:9]1[C:10]([CH3:16])=[N:11][CH:12]=[C:13]([Br:17])[C:14]=1[OH:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 27264163-(BENZYLOXY)-2-METHYL-4(1H)-PYRIDINONE

Product 1

HCID 178432655HCID 178432655, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The above compound 3 (129 g, 599 mmol) was suspended in acetonitrile (1300 ml), and N-bromosuccinic acid imide (117 g, 659 mmol) was added, followed by stirring at room temperature for 90 minutes. Precipitated crystals were filtered, and washed with acetonitrile and diethyl ether to obtain 3-benzyloxy-5-bromo-2-methyl-pyridine-4-ol 4 (154 g, 88%) as a colorless crystal. NMR (DMSO-d6) δ: 2.06 (3H, s), 5.04 (2H, s), 7.32-7.42 (5H, m), 8.03 (1H, d, J=5.5 Hz), 11.82 (1H, brs).

Workup

  1. customPrecipitated crystals
  2. filtrationwere filtered
  3. washwashed with acetonitrile and diethyl ether

Sources & evidence

ORD record
ord-72e030fbeb2e4051ab52993b4bb7564d
Source dataset
uspto-grants-2016_03
Patent number
US09273065B2

Reaction notes

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