Phosphoric Acid → HCID 13409282, compound

HRID 1980538Notes

Reaction equation

HRID 1980538 reaction equation
[C:1]1([C:7]2[NH:8][C:9]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O:19][C:20](=[O:22])[CH3:21])(=O)C.P(=O)(O)(O)O>C(O)(=O)C>[C:1]1([C:7]2[NH:8][C:9]3[C:14]([C:15]=2[C:1]2[CH2:6][CH2:5][CH:21]([C:20]([OH:19])=[O:22])[CH2:3][CH:2]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 7918Acetic AnhydrideHCID 136982-Phenylindole

Product 1

HCID 13409282HCID 13409282, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 100 g (0.52 mol) of 2-phenylindole, 80.8 g (0.57 mol) of 4-cyclohexanonecarboxylic acid, 518 mL of acetic acid, 103.6 mL of acetic anhydride and 25.9 mL of 85% phosphoric acid was stirred at room temperature for 3 days and then chilled in an ice bath to 20° C. The precipitate that resulted was collected, washed with water, pressed dry, taken up in ether, and this solution was washed with water three times and with brine one time, dried over magnesium sulfate, charcoaled, evaporated at 200 mL, and let stand for 2 days to give a precipitate. This precipitate was collected and combined with a second crop to give 72.7 g (44%) of 4-(2-phenyl-1H-indol-3-yl)-3-cyclohexene-1-carboxylic acid, m.p. 178°-179° C. A small portion was recrystallized from acetonitrile, m.p. 180°-183° C.

Workup

  1. temperaturechilled in an ice bath to 20° C
  2. customThe precipitate that resulted
  3. customwas collected
  4. washwashed with water
  5. custompressed dry
  6. washthis solution was washed with water three times and with brine one time
  7. dry with materialdried over magnesium sulfate
  8. customevaporated at 200 mL
  9. waitlet stand for 2 days
  10. customto give a precipitate
  11. customThis precipitate was collected

Sources & evidence

ORD record
ord-43dc18154e3f41398dbd3eadf6ae868f
Source dataset
uspto-grants-1985_04
Patent number
US04510158

Reaction notes

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