Ethyl formate → 7,8-Dimethoxy-2-formyl-5-phenyl-1,2,3,4,5,6-hexahydro-benzo[h]isoquinoline

HRID 54154Notes

Reaction equation

HRID 54154 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[CH2:9][CH:10]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:11]3[CH2:12][CH2:13][NH:14][CH2:15][C:16]=3[C:7]=2[CH:6]=[CH:5][C:4]=1[O:23][CH3:24].[CH:25](OCC)=[O:26]>C1COCC1>[CH3:1][O:2][C:3]1[C:8]2[CH2:9][CH:10]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:11]3[CH2:12][CH2:13][N:14]([CH:25]=[O:26])[CH2:15][C:16]=3[C:7]=2[CH:6]=[CH:5][C:4]=1[O:23][CH3:24]

Participants

4

Reactant 2

HCID 8025Ethyl formateHCID 19961160HCID 19961160, compound

Product 1

HCID 199611837,8-Dimethoxy-2-formyl-5-phenyl-1,2,3,4,5,6-hexahydro-benzo[h]isoquinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the free base 7,8-dimethoxy-5-phenyl-1,2,3,4,5,6-hexahydrobenzo[h]isoquinoline, (390 mg, 1.2 mmol, from Example 200) in THF (25 mL) was added ethyl formate (40 mL). The resulting solution was heated at reflux for 17 hours, concentrated, and the concentrate was chased with THF. The crude product was used directly in the next step.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 17 hours
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6175600e0da8416ea5a76f5e77922ffe
Source dataset
uspto-grants-1997_04
Patent number
US05621133

Reaction notes

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