Water → HCID 11171569, compound

HRID 1633726Notes

Reaction equation

HRID 1633726 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=[O:12].[Cl:13]N1C(=O)CCC1=O.O>CN(C)C=O>[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([Cl:13])=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=[O:12]

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 115065055-Amino-3,4-dihydronaphthalen-1(2H)-one

Product 1

HCID 11171569HCID 11171569, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-amino-1-tetralone (Itoh, K. Chem. Pharm. Bull. (1984), 32, 130-151) (0.50 g, 3.1 mmol) in dimethylformamide (15 mL) was treated with N-chlorosuccinimide (0.49 g, 3.7 mmol), stirred for 60 hours, treated with water and extracted with ether (4×30 mL). The combined ether extracts were washed with brine, dried (Na2SO4) and concentrated. Purification of the residue on silica gel with ethyl acetate:hexanes 1:1 provided the desired product.

Workup

  1. extractionextracted with ether (4×30 mL)
  2. washThe combined ether extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customPurification of the residue on silica gel with ethyl acetate:hexanes 1:1

Sources & evidence

ORD record
ord-40b217c9864946208015c6be2ef01444
Source dataset
uspto-grants-2003_01
Patent number
US06503935B1

Reaction notes

Loading…