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

HRID 2234242Notes

Reaction equation

HRID 2234242 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:2]=1.C(O)(=O)C>CO>[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:16])([CH3:15])[CH3:17])[CH2:2]1

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 75.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-quinolinylcarbamic acid, 1,1-dimethylethyl ester (6.0 g, 24.56 mmol) in MeOH (150 mL) was added acetic acid (18 mL). The mixture was bubbled with argon for 15 min, then palladium hydroxide (20 weight % palladium on carbon) (1.2 g) was added. The resulting suspension was subjected to hydrogenation under 45 psi of pressure for 16 h, then filtered. The filtrate was concentrated and the residue taken in CH2Cl2. The resulting CH2Cl2 solution was washed with saturated aqueous NaHCO3, saturated aqueous NaCl, dried (Na2SO4) and concentrated. The residue was chromatographed (silica gel) eluting with EtOAc (0 to 50%) in hexanes to give 1A (4.6 g, 75% yield) as a white solid.

Workup

  1. customThe mixture was bubbled with argon for 15 min
  2. additionpalladium hydroxide (20 weight % palladium on carbon) (1.2 g) was added
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. washThe resulting CH2Cl2 solution was washed with saturated aqueous NaHCO3, saturated aqueous NaCl
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue was chromatographed (silica gel)
  9. washeluting with EtOAc (0 to 50%) in hexanes

Sources & evidence

ORD record
ord-6e65b1b731504b98af65383293dd1897
Source dataset
uspto-grants-2010_05
Patent number
US07709647B2

Reaction notes

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