Sodium Hydroxide → 3-[(1-Methylethyl)amino]-5-(pyridin-4-yl)thiophene-2-carboxylic acid

HRID 2363995Notes

Reaction equation

[CH3:1][CH:2]([NH:4][C:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[S:7][C:6]=1[C:16]([O:18]C)=[O:17])[CH3:3].[OH-].[Na+]>CO>[CH3:3][CH:2]([NH:4][C:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[S:7][C:6]=1[C:16]([OH:18])=[O:17])[CH3:1]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of methyl 3-[(1-methylethyl)amino]-5-(pyridin-4-yl)thiophene-2-carboxylate (0.250 g, 0.905 mmol) and 2 M sodium hydroxide (1.36 mL, 2.72 mmol) in methanol (5 mL) was heated at 70° C. for 3 h. Then, the reaction was cooled to room temperature and concentrated. The obtained residue was dissolved in water (5 mL) and acidified with 1 M HCl (2.7 mL) and 4 drops of acetic acid. The resulting yellow precipitate was collected by filtration, washed with water and dried to give the title compound (0.229 g, 96%) as a yellow solid:

Workup

temperatureThen, the reaction was cooled to room temperature
concentrationconcentrated
dissolutionThe obtained residue was dissolved in water (5 mL)
filtrationThe resulting yellow precipitate was collected by filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-18d14b7ce0e24f4691654ec2bbddf96b
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691828B2

Reaction notes

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