Hydrogen Bromide → 6-(Bromomethyl)isoquinoline hydrobromide

HRID 1858560Notes

Reaction equation

HRID 1858560 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11]O)=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[BrH:13].C(OCC)C>C(O)(=O)C>[BrH:13].[Br:13][CH2:11][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[CH:1]=[N:2][CH:3]=[CH:4]2

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 22126247Isoquinolin-6-ylmethanol

Product 1

HCID 221268166-(Bromomethyl)isoquinoline hydrobromideYield 73%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
70 °C

Procedure

A solution of 190 mg (1.19 mmol) of 6-isoquinoline-methanol in 1 ml of glacial acetic acid was treated with 2 ml of 30% HBr in glacial acetic acid and the mixture was heated at 70° C. for 45 minutes. The reaction mixture was cooled, treated with 20 ml of diethyl ether and stirred at 0° C. for 30 min. The resulting solid was filtered off, washed with diethyl ether and dried in a high vacuum. There was obtained 6-bromomethyl-isoquinoline hydrobromide (73% of theory) as a light brown solid; MS: 221, 223 (M)+.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationThe resulting solid was filtered off
  3. washwashed with diethyl ether
  4. customdried in a high vacuum

Sources & evidence

ORD record
ord-3bf450f3059b4b28b341ef0ce3c786e9
Source dataset
uspto-grants-2000_11
Patent number
US06150526

Reaction notes

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