Acetone → HCID 19626956, compound

HRID 1428837Notes

Reaction equation

HRID 1428837 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12]1.[Cl-].[NH4+].CC(C)=O.S([O-])([O-])(=O)=O.[Na+].[Na+]>[Zn].CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12]1

Participants

7

Reactant 4

HCID 180AcetoneHCID 24436Sodium SulfateHCID 25517Ammonium ChlorideHCID 47100857HCID 47100857, compound

Product 1

HCID 19626956HCID 19626956, compoundYield 96.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(2-chloro-4-nitro-phenyl)-1,2,3,4-tetrahydro-isoquinoline (1.4 g, 4.8 mmol), saturated aqueous ammonium chloride (5 mL), and acetone (20 mL) was cooled in an ice bath. Solid zinc powder (3.2 g, 48 mmol) was added in portions over 10 min with stirring. The ice bath was allowed to expire and the mixture was stirred for 16 h. EtOAc (200 mL) was then added, followed by anhydrous sodium sulfate (20 g). The mixture was stirred for 15 min, then filtered through a pad of silica gel, eluting with EtOAc. The resulting clear solution was concentrated to afford the titled compound (1.2 g, 96%). 1H NMR (500 MHz, CDCl3): 7.20-7.11 (m, 3H), 7.11-7.04 (m, 1H), 6.95 (d, J=8.5 Hz, 1H), 6.78 (d, J=2.7 Hz, 1H), 6.56 (dd, J=8.5, 2.7 Hz, 1H), 4.17 (s, 2H), 3.55 (s, 2H), 3.27 (t, J=5.8 Hz, 2H), 3.00 (t, J=5.8 Hz, 2H).

Workup

  1. temperaturewas cooled in an ice bath
  2. stirringthe mixture was stirred for 16 h
  3. stirringThe mixture was stirred for 15 min
  4. filtrationfiltered through a pad of silica gel
  5. washeluting with EtOAc
  6. concentrationThe resulting clear solution was concentrated

Sources & evidence

ORD record
ord-1cfed4a41de14c66bb3e86d7cf5fc517
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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