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

HRID 218746Notes

Reaction equation

HRID 218746 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-a934939e72a54a28a918c47e294f6f6b
Source dataset
uspto-grants-2012_06
Patent number
US08198454B2

Reaction notes

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