Boron → 1-Amino-6-hydroxy-3-methyl-isoquinoline

HRID 478702Notes

Reaction equation

HRID 478702 reaction equation
[B].[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:13]C)=[CH:10][CH:11]=2)[CH:6]=[C:5]([CH3:15])[N:4]=1>ClCCl>[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([OH:13])=[CH:10][CH:11]=2)[CH:6]=[C:5]([CH3:15])[N:4]=1

Participants

4

Reactant 2

HCID 5462311BoronHCID 180026781-Amino-6-methoxy-3-methylisoquinoline

Product 1

HCID 1356965981-Amino-6-hydroxy-3-methyl-isoquinolineYield 86.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Boron tribomide (4 mL) in 6 mL of dichloromethane was added dropwise to a stirred solution of 1-amino-6-methoxy-3-methylisoquinoline (2 g) in 10 mL of dichloromethane at 0° C. After stirring for 16 hours at ambient temperature the reaction mixture was poured on ice, the organic layer removed and the pH of the aqueous layer adjusted to pH 9 by adding concentrated aqueous ammonia. The precipitated material was collected by filtration and dried in vacuo to give 1.6 g of the title compound. ESI-MS: 175 (MH+).

Workup

  1. additionwas poured on ice
  2. customthe organic layer removed
  3. additionby adding concentrated aqueous ammonia
  4. filtrationThe precipitated material was collected by filtration
  5. customdried in vacuo

Sources & evidence

ORD record
ord-dfa60bbe59514229a62100649e0ddb43
Source dataset
uspto-grants-2003_11
Patent number
US06642253B2

Reaction notes

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