Formic Acid → HCID 21584384, compound

HRID 583291Notes

Reaction equation

HRID 583291 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 twice 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 twice 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-a07567cde75c48bdb2867905b5540c98
Source dataset
uspto-grants-1999_07
Patent number
US05929085

Reaction notes

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