Formic Acid → HCID 21295816, compound

HRID 35228Notes

Reaction equation

HRID 35228 reaction equation
[NH2:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][CH2:7][N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][C:12]([O:20][CH3:21])=[C:13]([O:18][CH3:19])[CH:14]=3)[CH:9]2[CH3:22])=[CH:4][CH:3]=1.[CH:25](O)=[O:26]>C1(C)C=CC=CC=1>[CH:25]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][C:12]([O:20][CH3:21])=[C:13]([O:18][CH3:19])[CH:14]=3)[CH:9]2[CH3:22])=[CH:23][CH:24]=1)=[O:26]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 53505Veradoline

Product 1

HCID 21295816HCID 21295816, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of N-(4-aminophenethyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline (18.5 g, 0.056 m) in toluene (200 ml) under nitrogen was added 97% formic acid (25 ml) and the mixture heated to reflux, collecting the toluene insoluble material in a Dean-Stark tube. After 25 ml had been collected (ca 1 hr) the mixture was cooled and analyzed by TLC to insure completion. The mixture was poured into 500 ml H2O and basified to pH 11 with 10% NaOH, then extracted with CHCl3 (3×250 ml) and the combined extracts dried over MgSO4. Evaporation of the solvent gave N-(4-formamidophenethyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline as an oil, 20.0 g (100% yield).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux
  3. customcollecting the toluene insoluble material in a Dean-Stark tube
  4. customAfter 25 ml had been collected (ca 1 hr) the mixture
  5. temperaturewas cooled
  6. additionThe mixture was poured into 500 ml H2O and basified to pH 11 with 10% NaOH
  7. extractionextracted with CHCl3 (3×250 ml)
  8. dry with materialthe combined extracts dried over MgSO4
  9. customEvaporation of the solvent

Sources & evidence

ORD record
ord-987576915bee49a8966fe04419f094f2
Source dataset
uspto-grants-1988_08
Patent number
US04766131

Reaction notes

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