Hydrogen Bromide → 3-[2-(3-Azabicyclo[3.2.2]non-3-yl)ethyl]-1,2,3,4-tetrahydro-7,8-dihydroxy-5H-[1]benzopyrano[3,4-c]pyridin-5-one dihydrobromide

HRID 1995302Notes

Reaction equation

HRID 1995302 reaction equation
Cl.Cl.[CH:3]12[CH2:11][CH2:10][CH:7]([CH2:8][CH2:9]1)[CH2:6][N:5]([CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][C:17]3[C:20]4[CH:28]=[CH:27][C:26]([O:29]C)=[C:25]([O:31]C)[C:21]=4[O:22][C:23](=[O:24])[C:16]=3[CH2:15]1)[CH2:4]2.[BrH:33]>C(O)(=O)C>[BrH:33].[BrH:33].[CH:3]12[CH2:9][CH2:8][CH:7]([CH2:10][CH2:11]1)[CH2:6][N:5]([CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][C:17]3[C:20]4[CH:28]=[CH:27][C:26]([OH:29])=[C:25]([OH:31])[C:21]=4[O:22][C:23](=[O:24])[C:16]=3[CH2:15]1)[CH2:4]2

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 204881493-[2-(3-Azabicyclo[3.2.2]non-3-yl)ethyl]-1,2,3,4-tetrahydro-7,8-dimethoxy-5H-[1]benzopyrano[3,4-c]pyridin-5-one dihydrochloride

Product 1

HCID 131890453-[2-(3-Azabicyclo[3.2.2]non-3-yl)ethyl]-1,2,3,4-tetrahydro-7,8-dihydroxy-5H-[1]benzopyrano[3,4-c]pyridin-5-one dihydrobromide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Prepared by the method described in Example 19 from 3-[2-(3-azabicyclo[3.2.2]non-3-yl)ethyl]-1,2,3,4-tetrahydro-7,8-dimethoxy-5H-[1]benzopyrano[3,4-c]pyridin-5-one dihydrochloride (1.3 g, 0.0027 moles) and aqueous 48% hydrobromic acid (25 ml) plus acetic acid cosolvent (25 ml). After washing with a small amount of warm acetic acid, the final product (0.90 g) had mp 310°-313° C.

Workup

  1. customPrepared by the method
  2. washAfter washing with a small amount of warm acetic acid

Sources & evidence

ORD record
ord-3e2973dfadab45e1a3e869f63206c1a5
Source dataset
uspto-grants-1983_09
Patent number
US04404138

Reaction notes

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