Acetic Acid → Boc-3-amino-1,2,3,4-tetrahydroquinoline

HRID 1019675Notes

Reaction equation

HRID 1019675 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1[CH:9]=[N:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C>CO>[C:1]([O:5][C:6](=[O:18])[NH:7][CH:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 65142936Tert-butyl N-(quinolin-3-YL)carbamate

Product 1

HCID 4460996Boc-3-amino-1,2,3,4-tetrahydroquinolineYield 68.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of XXII (6.0 g, 24.56 mmol) in 150 mL of MeOH was added acetic acid (18 mL). The mixture was bubbled with argon for 15 min, then palladium hydroxide (20% palladium on carbon, 1.2 g) was added to the flask. The resulting suspension was subjected to hydrogenation under 45 psi for 16 h before filtered. The filtrate was concentrated and the residue was dissolved in CH2Cl2. The resulting CH2Cl2 solution was washed with saturated NaHCO3, dried over Na2SO4 and concentrated. The residue was purified through silica gel to give (1,2,3,4-tetrahydro-quinoline-3-yl)-carbamic acid tert-butyl ester XXIII (4.2 g, 68%).

Workup

  1. customThe mixture was bubbled with argon for 15 min
  2. additionpalladium hydroxide (20% palladium on carbon, 1.2 g) was added to the flask
  3. filtrationbefore filtered
  4. concentrationThe filtrate was concentrated
  5. dissolutionthe residue was dissolved in CH2Cl2
  6. washThe resulting CH2Cl2 solution was washed with saturated NaHCO3
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customThe residue was purified through silica gel

Sources & evidence

ORD record
ord-d5957cb87614432aa60f04aec86f56cb
Source dataset
uspto-grants-2014_05
Patent number
US08716285B2

Reaction notes

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