Sodium Hydroxide → 4-[4-(1-Propylamino-cyclopropyl)-phenylethynyl]-benzoic acid

HRID 381120Notes

Reaction equation

HRID 381120 reaction equation
C([O:3][C:4](=[O:26])[C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3([NH:22][CH2:23][CH2:24][CH3:25])[CH2:21][CH2:20]3)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)C.[OH-].[Na+]>C(O)C.O1CCCC1>[CH2:23]([NH:22][C:19]1([C:16]2[CH:17]=[CH:18][C:13]([C:12]#[C:11][C:8]3[CH:7]=[CH:6][C:5]([C:4]([OH:26])=[O:3])=[CH:10][CH:9]=3)=[CH:14][CH:15]=2)[CH2:20][CH2:21]1)[CH2:24][CH3:25]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22568896Ethyl4-[4-(1-propylamino-cyclopropyl)-phenylethynyl]-benzoate2×

Product 1

HCID 98800674-[4-(1-Propylamino-cyclopropyl)-phenylethynyl]-benzoic acidYield 69%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Using General Procedure I; a solution of ethyl4-[4-(1-propylamino-cyclopropyl)-phenylethynyl]-benzoate (Compound 107, 40.0 mg, 0.12 mmol) in ethanol (3 mL) and tetrahydrofuran (3 mL) was treated with NaOH (160.0 mg, 4.0 mmols, 2.0 mL of a 2N aqueous solution) and stirred overnight at room temperature. Work-up afforded 25.0 mg (69%) of the title compound as a solid.

Sources & evidence

ORD record
ord-1d3209571e594105b60bf560340b31f9
Source dataset
uspto-grants-2001_10
Patent number
US06303785B1

Reaction notes

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