Ethanolamine → 1-Amino-5-bromoisoquinoline

HRID 875044Notes

Reaction equation

HRID 875044 reaction equation
CS(Cl)(=O)=O.[Br:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH:9]=[CH:10][N+:11]([O-])=[CH:12]2.C(C[NH2:21])O>N1C=CC=CC=1>[Br:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH:9]=[CH:10][N:11]=[C:12]2[NH2:21]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 31297Methanesulfonyl chlorideHCID 22665708Isoquinoline, 5-bromo-, 2-oxide

Product 1

HCID 337785661-Amino-5-bromoisoquinoline

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3.2 47 μl (0.61 mmol) of methanesulfonyl chloride is added dropwise with ice-cooling to a suspension of 112.0 mg (0.50 mmol) of 5-bromoisoquinoline 2-oxide in 0.48 ml of pyridine. The reaction mixture is stirred at room temperature for 18 hours. 685 μl of ethanolamine are then added dropwise with ice-cooling, and the mixture is stirred at room temperature for a further 4 hours. The reaction mixture is poured into ice-water and stirred for 30 minutes. The precipitate formed is filtered off with suction, washed with water and dried in vacuo: 5-bromoisoquinolin-1-ylamine as yellow crystals; HPLC/MS: 1.26 min, [M+H] 223/225.

Workup

  1. temperaturecooling
  2. stirringthe mixture is stirred at room temperature for a further 4 hours
  3. stirringstirred for 30 minutes
  4. customThe precipitate formed
  5. filtrationis filtered off with suction
  6. washwashed with water
  7. customdried in vacuo
  8. custom1.26 min, [M+H] 223/225

Sources & evidence

ORD record
ord-5d9cc60562594f949327dcbd510672fb
Source dataset
uspto-grants-2015_03
Patent number
US08981101B2

Reaction notes

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