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

HRID 1935915Notes

Reaction equation

HRID 1935915 reaction equation
[CH2:1]([NH:4][C:5]1([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]3[CH:26]=[CH:25][C:19]([C:20]([O:22]CC)=[O:21])=[CH:18][CH:17]=3)=[CH:10][CH:9]=2)[CH2:7][CH2:6]1)[CH2:2][CH3:3].[OH-].[Na+]>C(O)C.O1CCCC1>[CH2:1]([NH:4][C:5]1([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]3[CH:17]=[CH:18][C:19]([C:20]([OH:22])=[O:21])=[CH:25][CH:26]=3)=[CH:10][CH:9]=2)[CH2:6][CH2:7]1)[CH2:2][CH3:3]

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 ethyl 4-[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-de3f06a26fe9402597bf28d140db4f19
Source dataset
uspto-grants-2002_05
Patent number
US06387892B1

Reaction notes

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