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N-bromobutanimide → 7-Benzyloxy-1-bromo-4-hydroxy-isoquinoline-3-carboxylic acid ethyl ester

HRID 2077254
Notes
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Reaction equation

HRID 2077254 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:10]=2)=[O:5])[CH3:2].[Br:25]N1C(=O)CCC1=O>C(#N)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([Br:25])[C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:10]=2)=[O:5])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 671103537-Benzyloxy-4-hydroxy-isoquinoline-3-carboxylic acid ethyl ester

Product 1

HCID 866170887-Benzyloxy-1-bromo-4-hydroxy-isoquinoline-3-carboxylic acid ethyl esterYield 74.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of 2.48 g (7.67 mmol) of 7-benzyloxy-4-hydroxy-isoquinoline-3-carboxylic acid ethyl ester and 1.43 g (8.0 mmol) of N-bromosuccinimide in 25 mL of acetonitrile was heated to 70° C. for ten minutes. The reaction was cooled and a white solid precipitated out of solution. The solid was collected by filtration through a medium glass fritted filter and washed with cold acetonitrile to give 2.3 g of the title compound; MS (ESI+): 402.2, 404.2 e/z (M+1, 79Br/81Br)

Workup

  1. temperatureThe reaction was cooled
  2. customa white solid precipitated out of solution
  3. filtrationThe solid was collected by filtration through a medium glass fritted filter
  4. washwashed with cold acetonitrile

Sources & evidence

ORD record
ord-52cd69d795f34e3ea1b4058f53c36138
Source dataset
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07928120B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes