HCID 474636, compound → HCID 178435267, compound

HRID 1415668Notes

Reaction equation

HRID 1415668 reaction equation
[CH2:1]([CH:3]1[C:9]2[N:10]=[CH:11][CH:12]=[CH:13][C:8]=2[C:7](=[O:14])[N:6]([CH3:15])[C:5]2[CH:16]=[CH:17][C:18]([O:20]C)=[N:19][C:4]1=2)[CH3:2].C(=O)(O)[O-].[Na+]>C(O)(=O)C.Br>[CH2:1]([CH:3]1[C:9]2[N:10]=[CH:11][CH:12]=[CH:13][C:8]=2[C:7](=[O:14])[N:6]([CH3:15])[C:5]2[CH:16]=[CH:17][C:18]([OH:20])=[N:19][C:4]1=2)[CH3:2]

Participants

5

Reactant 2

HCID 474636HCID 474636, compoundHCID 516892Sodium Bicarbonate

Product 1

HCID 178435267HCID 178435267, compoundYield 102.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 260Hydrogen BromideSolvent

Procedure

A solution of 5,11-dihydro-11-ethyl-2-methoxy-5-methyl-dipyrido[3,2-b:2',3'-e]azepine-6-one (0.181 g) in acetic acid (1 mL) and 48% HBr in acetic acid (1 mL) was heated at 110° C. for 10 minutes. The mixture was cooled, neutralized with saturated sodium bicarbonate, and extracted with chloroform. The organic phase was dried, filtered and evaporated to give 5,11-dihydro-11-ethyl-2-hydroxy-5-methyl-dipyrido[3,2-b:2',3'-e]azepine-6-one (0.176 g) which was used directly in the next reaction.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with chloroform
  3. customThe organic phase was dried
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-494b257f28fc49e88ef601c9bf80968a
Source dataset
uspto-grants-1999_06
Patent number
US05908841

Reaction notes

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