Water → (2R)-6-iodochromane-2-carboxamide

HRID 47666Notes

Reaction equation

HRID 47666 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C@@H:7]([C:12]([OH:14])=O)[CH2:6][CH2:5]2.C([O-])(=O)C.[NH4+:19].O>CN(C)C=O>[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C@@H:7]([C:12]([NH2:19])=[O:14])[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 962WaterHCID 517165Ammonium AcetateHCID 9966213(2R)-6-Iodochromane-2-carboxylic acid

Product 1

HCID 9966188(2R)-6-iodochromane-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The crude carboxylic acid of Example 7 (30.4 g, 100 mmol) and CDl (19.5 g, 120 mmol) were stirred in N,N-dimethylformamide (300 mL) at room temperature for 2 hours to obtain a yellow solution. To this solution was then added ammonium acetate (23.1 g, 300 mmol). The resulting mixture was stirred for 3 hours. It was then cooled in an ice-water bath and water (400 mL) was then added dropwise to the reaction mixture to obtain a fine white precipitation which was stirred for 12 hours. The solid was collected by vacuum filtration, washed with water and dried by suction (25.8 g, 85%): 1H NMR (DMSO-d6) δ1.75-1.90 (m, 1H), 2.00-2.15 (m, 1H), 2.55-2.80 (m, 2H), 4.43-4.47 (dd, J=8.7, 3.3 Hz, 1H), 6.65 (d, J=8.1 Hz, 1H), 7.35 (m, 2H). CI-MS m/z 304 (M +H+).

Workup

  1. customto obtain a yellow solution
  2. temperatureIt was then cooled in an ice-water bath
  3. customto obtain
  4. customa fine white precipitation which
  5. stirringwas stirred for 12 hours
  6. filtrationThe solid was collected by vacuum filtration
  7. washwashed with water
  8. customdried by suction (25.8 g, 85%)

Sources & evidence

ORD record
ord-c2accae84f5b44a892a50b3de2dfa089
Source dataset
uspto-grants-2004_03
Patent number
US06699860B2

Reaction notes

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