Formic Acid → HCID 21584307, compound

HRID 369945Notes

Reaction equation

HRID 369945 reaction equation
[ClH:1].[CH3:2][CH:3]1[CH2:12][C:11]2[C:6](=[CH:7][C:8]([N+:13]([O-:15])=[O:14])=[CH:9][CH:10]=2)[CH2:5][NH:4]1.C=O.[CH:18](O)=O.C([O-])=O.[Na+]>O>[ClH:1].[CH3:18][N:4]1[CH:3]([CH3:2])[CH2:12][C:11]2[C:6](=[CH:7][C:8]([N+:13]([O-:15])=[O:14])=[CH:9][CH:10]=2)[CH2:5]1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 712FormaldehydeHCID 2723810Sodium FormateHCID 21584363HCID 21584363, compound

Product 1

HCID 21584307HCID 21584307, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 3-methyl-7-nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride (2.0 g, 8.75 mmol) in 37% formaldehyde (7.0 ml, 87.5 mmol) was added 96% formic acid (3.5 ml, 87.5 mmol) and sodium formate (0.60 g, 8.75 mmol). The mixture was heated at reflux for 1 h, cooled, dumped into basic water and extracted with ethyl acetate (3×50 ml). The combined extracts were washed with water, dried over magnesium sulfate, filtered, and concentrated to an oil. The oil was dissolved in ethanol and treated with isopropanol-HCl. The solids were collected by filtration (2.0 g, 95%), m.p. 242-244° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 h
  3. temperaturecooled
  4. extractionextracted with ethyl acetate (3×50 ml)
  5. washThe combined extracts were washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to an oil
  9. dissolutionThe oil was dissolved in ethanol
  10. additiontreated with isopropanol-HCl
  11. filtrationThe solids were collected by filtration (2.0 g, 95%), m.p. 242-244° C.

Sources & evidence

ORD record
ord-99aaec053a37491aaf8d7c3fb7b45a75
Source dataset
uspto-grants-2000_10
Patent number
US06140322

Reaction notes

Loading…