Formic Acid → N-(4-formamidophenethyl)-1,2,3,4-tetrahydro-6-methoxy-1-methylisoquinoline

HRID 35239Notes

Reaction equation

HRID 35239 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][CH2:7][N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH3:19])[CH:14]=3)[CH:9]2[CH3:20])=[CH:4][CH:3]=1.[CH:23](O)=[O:24]>C1(C)C=CC=CC=1>[CH:23]([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][CH:12]=[C:13]([O:18][CH3:19])[CH:14]=3)[CH:9]2[CH3:20])=[CH:21][CH:22]=1)=[O:24]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 14230290N-(4-aminophenethyl)-1,2,3,4-tetrahydro-6-methoxy-1-methylisoquinoline

Product 1

HCID 14230294N-(4-formamidophenethyl)-1,2,3,4-tetrahydro-6-methoxy-1-methylisoquinoline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of N-(4-aminophenethyl)-1,2,3,4-tetrahydro-6-methoxy-1-methylisoquinoline (16.8 g, 0.057 m) in 800 ml toluene was added formic acid (25.0 g, 0.5 m). The reaction was brought to reflux, and water was collected by a Dean-Stark apparatus. After 1 hour, the reaction was poured into ice water (500 g) and basified to pH 11-12 with 10% NaOH. The toluene layer was separated, and the aqueous layer was extracted further with toluene (1×200 ml) and then with chloroform (2×200 ml). The organic extracts were combined, dried and concentrated to an oil. The oil was dissolved in 100 ml ether and a solid formed which was filtered off and dried to give N-(4-formamidophenethyl)-1,2,3,4-tetrahydro-6 -methoxy-1-methylisoquinoline, wt. 12.0 g (71%), m.p. 93°-96°.

Workup

  1. temperatureto reflux
  2. customwater was collected by a Dean-Stark apparatus
  3. additionthe reaction was poured into ice water (500 g)
  4. customThe toluene layer was separated
  5. extractionthe aqueous layer was extracted further with toluene (1×200 ml)
  6. customdried
  7. concentrationconcentrated to an oil
  8. dissolutionThe oil was dissolved in 100 ml ether
  9. customa solid formed which
  10. filtrationwas filtered off
  11. customdried

Sources & evidence

ORD record
ord-8a7abec084394b899e7192463b15817c
Source dataset
uspto-grants-1988_08
Patent number
US04766131

Reaction notes

Loading…