Formic Acid → HCID 21584384, compound

HRID 369990Notes

Reaction equation

HRID 369990 reaction equation
[ClH:1].[N+:2]([C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][NH:11][CH:12]2[CH2:15][CH2:16][CH3:17])=[CH:7][CH:6]=1)([O-:4])=[O:3].[OH-].[NH4+].Cl.[CH:21](O)=O>C=O.C(O)C>[ClH:1].[CH3:21][N:11]1[CH2:10][CH2:9][C:8]2[C:13](=[CH:14][C:5]([N+:2]([O-:4])=[O:3])=[CH:6][CH:7]=2)[CH:12]1[CH2:15][CH2:16][CH3:17]

Participants

7

Reactant 4

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 21584287HCID 21584287, compound

Product 1

HCID 21584384HCID 21584384, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 712FormaldehydeSolvent

Procedure

A solution of 7-nitro-1-propyl-1,2,3,4-tetrahydroisoquinoline hydrochloride (2.50 g, 9.74 mmol) in formic acid (6.0 ml) and aqueous formaldehyde (9.0 ml) was heated at reflux for 1 h. The cooled solution was poured onto ice, made basic with concentrated ammonium hydroxide, and extracted with dichloromethane. The dried (magnesium sulfate) extracts were concentrated to give an oil which was taken up in ethanol and hydrochloric acid in ethanol was added until acidic. Since no precipitate formed on standing, the solvent was evaporated in vacuo and the residue was taken up in isopropanol (35 ml) and allowed to stand for several hours. The precipitate was collected to give the title compound (1.30 g, 49%) as an off-white solid, m.p. 198.5-200.5° C.

Workup

  1. temperatureat reflux for 1 h
  2. additionThe cooled solution was poured onto ice
  3. extractionextracted with dichloromethane
  4. dry with materialThe dried (magnesium sulfate) extracts
  5. concentrationwere concentrated
  6. customto give an oil which
  7. customSince no precipitate formed
  8. customthe solvent was evaporated in vacuo
  9. waitto stand for several hours
  10. customThe precipitate was collected

Sources & evidence

ORD record
ord-6101cf52f8144ed0a37178abe30400b7
Source dataset
uspto-grants-2000_10
Patent number
US06140322

Reaction notes

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