Hydrogen Bromide → HCID 68132713, compound

HRID 268300Notes

Reaction equation

HRID 268300 reaction equation
[ClH:1].C[O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=3)[CH2:9][N:10]([CH3:14])[CH2:11]2)=[CH:6][CH:5]=1.Br>>[ClH:1].[CH3:14][N:10]1[CH2:9][CH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=2)[C:7]2[C:12](=[CH:13][C:4]([OH:3])=[CH:5][CH:6]=2)[CH2:11]1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 68132955HCID 68132955, compound

Product 1

HCID 68132713HCID 68132713, compound

Procedure

The free base obtained from 4.0 g. of rac.-1,2,3,4-tetrahydro-7-methoxy-2-methyl-4-(3-nitrophenyl)isoquinoline hydrochloride is heated to 150°C. (bath-temperature) for 1.5 hours with 60 ml. of 48% hydrogen bromide solution. After concentration and partitioning between sodium bicarbonate solution and ethyl acetate, acidification with ethanolic hydrogen chloride, crystallization with ether and recrystallization from methanol-ether, there is obtained colorless rac.-1,2,3,4-tetrahydro-2-methyl-4-(3-nitrophenyl)-7-isoquinolinol hydrochloride of melting point 257°-258°C. (dec.).

Workup

  1. customThe free base obtained from 4.0 g
  2. concentrationAfter concentration
  3. custompartitioning between sodium bicarbonate solution and ethyl acetate, acidification with ethanolic hydrogen chloride, crystallization with ether and recrystallization from methanol-ether

Sources & evidence

ORD record
ord-b91bbd04fda24e05aeb8a95a57d02b03
Source dataset
uspto-grants-1976_03
Patent number
US03947456

Reaction notes

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