Sodium Hydroxide → HCID 68846281, compound

HRID 1889277Notes

Reaction equation

HRID 1889277 reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]=1[NH:15][CH2:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:4].[OH-].[Na+]>CO.C1COCC1>[C:19]1([CH2:18][CH2:17][CH2:16][NH:15][C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:13]=[CH:14][C:5]=2[C:3]([OH:4])=[O:2])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68842538HCID 68842538, compound

Product 1

HCID 68846281HCID 68846281, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

48 mg 1-(3-phenyl-propylamino)-naphthalene-2-carboxylic acid methyl ester were reacted with 0.14 ml of 2 M sodium hydroxide in 1 ml methanol and 1 ml of THF at 65° C. for 2 h. The organic solvents were then removed in vacuo, and the residue was taken up in water and ethyl acetate. The pH was brought to 3-4 with 2 M hydrochloric acid. The layers were separated and the aqueous layer was extracted with ethyl acetate twice. The combined organic layers were dried over sodium sulphate, and concentrated. After purification by chromatography on silica (ethyl acetate/heptane) 18 mg of 1-(3-phenyl-propylamino)-naphthalene-2-carboxylic acid were obtained.

Workup

  1. customThe organic solvents were then removed in vacuo
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate twice
  4. dry with materialThe combined organic layers were dried over sodium sulphate
  5. concentrationconcentrated
  6. customAfter purification by chromatography on silica (ethyl acetate/heptane) 18 mg of 1-(3-phenyl-propylamino)-naphthalene-2-carboxylic acid
  7. customwere obtained

Sources & evidence

ORD record
ord-3a9cbef129cd46bea6f89aca59fda099
Source dataset
uspto-grants-2013_08
Patent number
US08501981B2

Reaction notes

Loading…