Water → tert-Butyl 6-chloro-1,2,3,4-tetrahydroquinolin-3-ylcarbamate

HRID 2234249Notes

Reaction equation

HRID 2234249 reaction equation
[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]([CH3:17])([CH3:16])[CH3:15])[CH2:2]1.[Cl:19]N1C(=O)CCC1=O.O>C(#N)C>[Cl:19][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[NH:1][CH2:2][CH:3]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16])[CH2:4]2

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 4460996Boc-3-amino-1,2,3,4-tetrahydroquinoline

Product 1

HCID 59297067tert-Butyl 6-chloro-1,2,3,4-tetrahydroquinolin-3-ylcarbamateYield 58%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of tert-butyl 1,2,3,4-tetrahydroquinolin-3-yl-carbamate (28.3 g, 114 mmol), prepared as described in Example 1A, in acetonitrile (240 mL) at RT was added dropwise a solution of N-chlorosuccinimide (15.22 g, 114 mmol) in acetonitrile (240 mL). After addition, the reaction mixture was stirred for 6 h, then water (500 mL) added. The mixture was extracted with EtOAc (2×500 mL). The combined organics were washed with saturated aqueous NaCl, dried Na2SO4) and concentrated. The residue was chromatographed (silica gel) eluting with EtOAc/hexanes (1:5 ratio) to give the title compound (10.6 g, 58% yield) as a white solid.

Workup

  1. additionAfter addition
  2. extractionThe mixture was extracted with EtOAc (2×500 mL)
  3. washThe combined organics were washed with saturated aqueous NaCl, dried Na2SO4) and
  4. concentrationconcentrated
  5. customThe residue was chromatographed (silica gel)
  6. washeluting with EtOAc/hexanes (1:5 ratio)

Sources & evidence

ORD record
ord-d8a1ef6e64934296b8ee6ff8272f7914
Source dataset
uspto-grants-2010_05
Patent number
US07709647B2

Reaction notes

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