Formic Acid → HCID 21584276, compound

HRID 369953Notes

Reaction equation

HRID 369953 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-638d7486b4e54a18866d15d24b49690c
Source dataset
uspto-grants-2000_10
Patent number
US06140322

Reaction notes

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