Hydrochloric Acid → HCID 9931509, compound

HRID 1860298Notes

Reaction equation

HRID 1860298 reaction equation
C([O:3][C:4](=[O:32])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:22][C:21]3[C:20]([CH3:24])([CH3:23])[CH2:19][CH2:18][C:17]([CH3:26])([CH3:25])[C:16]=3[CH2:15]2)=[O:13])=[N:7][CH:6]=1)C.[OH-].[K+].Cl>C(O)C.O>[CH3:25][C:17]1([CH3:26])[CH2:18][CH2:19][C:20]([CH3:23])([CH3:24])[C:21]2[CH2:22][C:14]([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])([C:12]([NH:11][C:8]3[CH:9]=[CH:10][C:5]([C:4]([OH:32])=[O:3])=[CH:6][N:7]=3)=[O:13])[CH2:15][C:16]1=2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 69759882HCID 69759882, compound

Product 1

HCID 9931509HCID 9931509, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The ester was dissolved in 20 ml of ethanol and treated with a solution of 1 g of KOH (potassium hydroxyde) in 2 ml of water. After 2 hours at 40° C. the reaction mixture was poured on ice/water, acidified with 2 N HCl and extracted with ethyl acetate. The organic phase was dried (Na2SO4) and the solvent evaporated. The residue was crystallized from ethyl acetate/pentane and gave 0.6 g of 6-[(4,4,7,7-tetramethyl-2-pentyl-2,3,4,5,6,7-hexahydro-1H-indene-2-carbonyl)-amino]-nicotinic acid as colorless crystals, m. p. 172-174° C.

Workup

  1. additionAfter 2 hours at 40° C. the reaction mixture was poured on ice/water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. customthe solvent evaporated
  5. customThe residue was crystallized from ethyl acetate/pentane

Sources & evidence

ORD record
ord-42f7dc94d8284550b0cb9e9a7b4c094a
Source dataset
uspto-grants-2003_03
Patent number
US06528677B1

Reaction notes

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