N-bromobutanimide → HCID 178487833, compound

HRID 2279424Notes

Reaction equation

HRID 2279424 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][O:10][C:11]1[N:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]=[CH:16][CH:15]=[C:14]2[OH:21]>C(O)(=O)C>[Br:1][C:15]1[CH:16]=[N:17][C:18]2[C:13]([C:14]=1[OH:21])=[N:12][C:11]([O:10][CH3:9])=[CH:20][CH:19]=2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 178487891HCID 178487891, compound

Product 1

HCID 178487833HCID 178487833, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
15 °C

Procedure

N-Bromosuccinimide (263 mg, 1.48 mmol, 1.3 eq) is added at 15° C. to a stirred solution of 6-methoxy-[1,5]naphthyridin-4-ol (200 mg, 1.14 mmol, 1.0 eq) in acetic acid (3 mL). After 30 minutes stirring at 15° C., the reaction mixture is allowed to come at room temperature and the resulting cake is filtered, washed with acetic acid and dried to afford 3-bromo-6-methoxy-[1,5]naphthyridin-4-ol as an off-white solid (280 mg, 97% yield).

Workup

  1. customto come at room temperature
  2. filtrationthe resulting cake is filtered
  3. washwashed with acetic acid
  4. customdried

Sources & evidence

ORD record
ord-485e4ec02d84414d902e065ee15a946b
Source dataset
uspto-grants-2015_09
Patent number
US09133219B2

Reaction notes

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