Sodium Carbonate → HCID 68132942, compound

HRID 268299Notes

Reaction equation

HRID 268299 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH:21]=[CH:22][CH:23]=1)[CH2:7][NH:8][CH2:9][CH:10](O)[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C>[ClH:1].[CH3:2][O:3][C:4]1[CH:23]=[CH:22][CH:21]=[C:6]2[C:5]=1[CH:10]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=1)[CH2:9][NH:8][CH2:7]2

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 68132641HCID 68132641, compound

Product 1

HCID 68132942HCID 68132942, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

55 G. of rac.-α-{[(3-methoxybenzyl)amino]methyl}-3-nitrobenzyl alcohol hydrochloride and 165 g. of polyphosphoric acid (84.1% P2O5) are heated to 100° for 45 minutes. After the addition of a little ice and ethyl acetate the mixture is made alkaline with sodium carbonate and extracted. The ethyl acetate extract (46 g.) is chromatographed on 3.7 kg. of silica gel. With ether-acetone-diethylamine 19:1:1 there are eluted two uniform main fractions of 7.0 g. and 22.2 g. After acidification with ethanolic hydrochloric acid, crystallization and recrystallization from methanol-ether, from the first fraction there is obtained rac.-1,2,3,4-tetrahydro-5-methoxy-4-(3-nitrophenyl)isoquinoline hydrochloride, m.p. 217°-219° and from the second rac.-1,2,3,4-tetrahydro-7-methoxy-4-(3-nitrophenyl)isoquinoline hydrochloride, m.p. 253°-255°.

Workup

  1. extractionextracted
  2. extractionThe ethyl acetate extract (46 g.)
  3. customis chromatographed on 3.7 kg
  4. washWith ether-acetone-diethylamine 19:1:1 there are eluted two uniform main fractions of 7.0 g
  5. customAfter acidification with ethanolic hydrochloric acid, crystallization and recrystallization from methanol-ether

Sources & evidence

ORD record
ord-7a0d1a64afc54a06a6ee3b42a763ae3b
Source dataset
uspto-grants-1976_03
Patent number
US03947456

Reaction notes

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