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

HRID 1481676Notes

Reaction equation

HRID 1481676 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.[CH3:13]C(O)=O.[BH3-]C#N.[Na+]>CO>[CH3:13][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

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tetrahydroquinoline (4.0 g, 30.0 mmol) in MeOH (60 mL) was added CH2O (37% aqueous solution, 2.7 mL, 36.3 mmol, 1.2 eq) and HOAc (1.73 mL, 30.0 mmol, 1.0 eq). The mixture was stirred at room temperature for 10 min then was cooled to 0° C. before NaBH3CN (1.98 g, 31.5 mmol, 1.05 eq) was added. After 1 h, the solvent was removed under reduced pressure. The reaction was quenched with saturated aqueous NaHCO3 then extracted with CH2Cl2 (5×30 mL). The combined organic layers were dried over Na2SO4 then concentrated to give a crude product which was used in the next step without further purification.

Workup

  1. additionwas added
  2. waitAfter 1 h
  3. customthe solvent was removed under reduced pressure
  4. customThe reaction was quenched with saturated aqueous NaHCO3
  5. extractionthen extracted with CH2Cl2 (5×30 mL)
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. concentrationthen concentrated

Sources & evidence

ORD record
ord-3a93df86b66a4fc88911f234f0133fd4
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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