N-bromobutanimide → HCID 86617066, compound

HRID 706143Notes

Reaction equation

HRID 706143 reaction equation
[CH2:1]([O:5][C:6]([C:8]1[N:9]=[CH:10][C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][C:14]([O:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4].[Br:28]N1C(=O)CCC1=O>CC#N>[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10]([Br:28])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][C:14]([O:19][C:20]1[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=1)=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 66712699HCID 66712699, compound

Product 1

HCID 86617066HCID 86617066, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To mixture of 4-Hydroxy-6-(4-methoxy-phenoxy)-isoquinoline-3-carboxylic acid butyl ester (1.837 g, 5 mmol; for preparation, see example 28b) and N-bromosuccinimide (1.079 g, 6 mmol) was added anhydrous MeCN with stirring. After ca. 10 min another portion of MeCN (3 mL) was added and stirring continued for 20 min. The mixture was then partitioned between water (100 mL) and CCl4 (100 mL). The organic phase was separated, dried over MgSO4 and concentrated in vacuo. The residue was recrystallized from EtOAc to give the title compound as white needles (1.345 g); MS-(+)-ion: M+1, 79Br/81Br=445.8 and 447.8.

Workup

  1. stirringstirring
  2. customThe mixture was then partitioned between water (100 mL) and CCl4 (100 mL)
  3. customThe organic phase was separated
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was recrystallized from EtOAc

Sources & evidence

ORD record
ord-55728a18eb75428b95b35a857a65c89f
Source dataset
uspto-grants-2015_11
Patent number
US09174976B2

Reaction notes

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