Acetic Acid → 1,2,3,4-Tetrahydro-1-methylquinoline

HRID 649199

Reaction equation

HRID 649199 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.C=O.[BH3-][C:14]#N.[Na+].C(O)(=O)C>CC#N.CCOCC>[CH3:14][N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 176Acetic Acid2×HCID 712FormaldehydeHCID 694601,2,3,4-TetrahydroquinolineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 681091,2,3,4-Tetrahydro-1-methylquinoline

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

1,2,3,4-tetrahydroquinoline (2.0 g, 0.0015 mol) and formaldehyde (12 ml of 38% aqueous, 0.015 mol) were combined in 60 ml CH3CN. NaBH3CN (2.85 g) and then, over a 10 minute period, glacial acetic acid (1.50 ml) were added and the mixture stirred 2 hours, at which time additional acetic acid (0.5 ml) was added. After stirring an additional 30 minutes, the reaction mixture was poured into 200 ml ether, washed 3×30 ml IN NaOH, dried (K2CO3) and stripped in vacuo to yield title product, 2.27 g.

Workup

  1. additionwas added
  2. washwashed 3×30 ml IN NaOH
  3. dry with materialdried (K2CO3)

Sources & evidence

ORD record
ord-85419eeb82a746f786df9b99a5e207be
Source dataset
uspto-grants-1988_04
Patent number
US04738972

Linked notes

Loading…