Water → 8-amino-N-[(1-ethylpyrazol-4-yl)methyl]-N-(4-isopropylphenyl)chroman-4-carboxamide

HRID 2265517Notes

Reaction equation

HRID 2265517 reaction equation
O.[Cl-].[NH4+].[CH2:4]([N:6]1[CH:10]=[C:9]([CH2:11][N:12]([C:28]2[CH:33]=[CH:32][C:31]([CH:34]([CH3:36])[CH3:35])=[CH:30][CH:29]=2)[C:13]([CH:15]2[C:24]3[C:19](=[C:20]([N+:25]([O-])=O)[CH:21]=[CH:22][CH:23]=3)[O:18][CH2:17][CH2:16]2)=[O:14])[CH:8]=[N:7]1)[CH3:5]>C(O)C.[Fe]>[NH2:25][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]2[C:19]=1[O:18][CH2:17][CH2:16][CH:15]2[C:13]([N:12]([CH2:11][C:9]1[CH:8]=[N:7][N:6]([CH2:4][CH3:5])[CH:10]=1)[C:28]1[CH:33]=[CH:32][C:31]([CH:34]([CH3:36])[CH3:35])=[CH:30][CH:29]=1)=[O:14]

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 59597278N-[(1-ethylpyrazol-4-yl)methyl]-N-(4-isopropylphenyl)-8-nitrochroman-4-carboxamide

Product 1

HCID 595972328-amino-N-[(1-ethylpyrazol-4-yl)methyl]-N-(4-isopropylphenyl)chroman-4-carboxamideYield 78.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent2×

Procedure

To a mixed solvent of ethanol (43 mL) and water (18 mL) were added iron (0.43 g) and ammonium chloride (0.06 g), and a solution of N-[(1-ethylpyrazol-4-yl)methyl]-N-(4-isopropylphenyl)-8-nitrochroman-4-carboxamide (0.9 g) in ethanol (10 mL) was added dropwise with heating and stirring at 50° C.-70° C. After stirring at 50° C.-70° C. for 3 hr, the reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography to give 8-amino-N-[(1-ethylpyrazol-4-yl)methyl]-N-(4-isopropylphenyl)chroman-4-carboxamide (0.66 g).

Workup

  1. temperaturewith heating
  2. stirringAfter stirring at 50° C.-70° C. for 3 hr
  3. customthe reaction mixture was partitioned between water and ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3acd20ad90c342aa89feb5bb588d4229
Source dataset
uspto-grants-2010_12
Patent number
US07855297B2

Reaction notes

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