Ammonia → 2-(2-Chloro-6-dimethylaminomethyl-naphthalen-1-yl)acetamide

HRID 639196Notes

Reaction equation

HRID 639196 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:12][N:13]([CH3:15])[CH3:14])[CH:8]=2)[C:3]=1[CH2:16][C:17]([OH:19])=O.[NH3:20]>CN(C=O)C>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:12][N:13]([CH3:15])[CH3:14])[CH:8]=2)[C:3]=1[CH2:16][C:17]([NH2:20])=[O:19]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 68706916(2-Chloro-6-dimethylaminomethyl-naphthalen-1-yl)-acetic acid

Product 1

HCID 687039782-(2-Chloro-6-dimethylaminomethyl-naphthalen-1-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2-Chloro-6-dimethylaminomethyl-naphthalen-1-yl)-acetic acid (276 mg, 0.99 mmol) is dissolved under an atmosphere of argon in DMF (3 ml). 1,1-Carbonyl diimidazole (177 mg, 1.09 mmol) is added, and the clear solution is stirred at RT for 3 h. A conc. aqueous solution of ammonia (25%, 6 ml) is added, and stirring is continued for 10 minutes at RT. TLC analysis indicates complete consumption of starting material. The reaction mixture is poured on water. The aqueous layer is extracted with EtOAc, which is then washed with brine and dried over Na2SO4. After removal of solvent, the residue is found to be pure title compound, with no need of purification. 1H NMR (d6-DMSO, 400 MHz): δ 2.18 (s, 6H), 3.53 (s, 2H), 4.08 (s, 2H), 6.96-7.08 (br, 2H), 7.48-7.68 (m, 2H), 7.78-7.86 (m, 2H), 7.96-8.00 (d, J=10 Hz, 1H). ES+-MS: 277.3, 279.2 [M+H]+.

Workup

  1. stirringstirring
  2. waitis continued for 10 minutes at RT
  3. customconsumption of starting material
  4. additionThe reaction mixture is poured on water
  5. extractionThe aqueous layer is extracted with EtOAc, which
  6. washis then washed with brine
  7. dry with materialdried over Na2SO4
  8. customAfter removal of solvent
  9. customwith no need of purification

Sources & evidence

ORD record
ord-8714d1cfa9e54d509650bdbceb4f0110
Source dataset
uspto-grants-2010_04
Patent number
US07691861B2

Reaction notes

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