Formic Acid → HCID 21584276, compound

HRID 583253Notes

Reaction equation

HRID 583253 reaction equation
[ClH:1].[CH2:2]([CH:4]1[CH2:13][C:12]2[C:7](=[CH:8][C:9]([N+:14]([O-:16])=[O:15])=[CH:10][CH:11]=2)[CH2:6][NH:5]1)[CH3:3].[CH:17](O)=O.[OH-].[Na+].Cl.C(O)C>C=O.O>[ClH:1].[CH2:2]([CH:4]1[CH2:13][C:12]2[C:7](=[CH:8][C:9]([N+:14]([O-:16])=[O:15])=[CH:10][CH:11]=2)[CH2:6][N:5]1[CH3:17])[CH3:3]

Participants

7

Reactant 4

HCID 284Formic AcidHCID 14798Sodium HydroxideHCID 21584375HCID 21584375, compoundHCID 21887872Ethanol hydrochloride

Product 1

HCID 21584276HCID 21584276, compound

Reagents, catalysts & solvents 2

HCID 712FormaldehydeSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 3-ethyl-7-nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride (4.0 g, 8 mmol) in formaldehyde (15 ml) was added formic acid (7.0 ml) and the reaction was then refluxed for 1.5 h. The reaction was cooled and poured into water (300 ml) and made basic with 50% NaOH. The aqueous phase was then extracted with dichloromethane (3×100 ml), and the organic phase dried over MgSO4. Evaporation of the solvent yielded a crude oil. A hydrochloride salt was made from ethanol-HCl, (1.8 g), m.p. 240-241° C.

Workup

  1. temperaturethe reaction was then refluxed for 1.5 h
  2. temperatureThe reaction was cooled
  3. extractionThe aqueous phase was then extracted with dichloromethane (3×100 ml)
  4. dry with materialthe organic phase dried over MgSO4
  5. customEvaporation of the solvent
  6. customyielded a crude oil

Sources & evidence

ORD record
ord-5fe20491d49e49cab359126a3d95d5ef
Source dataset
uspto-grants-1999_07
Patent number
US05929085

Reaction notes

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