3-bromo-2-methoxy-5-methyl-6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepine → HCID 178430478, compound

HRID 597911Notes

Reaction equation

HRID 597911 reaction equation
[Br:1][C:2]1[C:13]([O:14]C)=[N:12][C:5]2[CH2:6][CH2:7][NH:8][CH2:9][CH:10]([CH3:11])[C:4]=2[CH:3]=1>Br>[Br:1][C:2]1[C:13]([OH:14])=[N:12][C:5]2[CH2:6][CH2:7][NH:8][CH2:9][CH:10]([CH3:11])[C:4]=2[CH:3]=1

Participants

3

Reactant 1

HCID 236537293-bromo-2-methoxy-5-methyl-6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepine

Product 1

HCID 178430478HCID 178430478, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

3-Bromo-2-methoxy-5-methyl-6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepine (152 mg, 414 μmol) in 48% aq. HBr (50 ml) was heated at reflux for 1 h. After neutralization with Na2CO3 and concentration in vacuo, the residue was purified by column chromatography and furnished 13.3 mg (13%) of 3-bromo-5-methyl-6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepin-2-ol. 1H-NMR (CDCl3) δ 7.68 (s, 1H), 3.08-2.77 (m, 7H), 1.26 (d, 3H) ppm.

Workup

  1. temperatureat reflux for 1 h
  2. concentrationAfter neutralization with Na2CO3 and concentration in vacuo
  3. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-bd72a6b4ef25421492961fec7bb1051d
Source dataset
uspto-grants-2011_03
Patent number
US07897595B2

Reaction notes

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