Pyridine → 2-Cyclopropylamino-4,5-difluorobenzoic acid

HRID 973786

Reaction equation

Cl[C:2]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH:13]1([NH2:16])[CH2:15][CH2:14]1.N1C=CC=CC=1.[OH-].[Na+]>CN(C)C(=O)C.[Cu]I.O>[CH:13]1([NH:16][C:2]2[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])[CH2:15][CH2:14]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a 10 ml resealable pressure reaction flask equipped with a magnetic stirrer and teflon septum cap was charged a solution of 1.0 g (5.19 mmol) 2-chloro-4,5-difluorobenzoic acid, 792 μl (11.43 mmol) cyclopropylamine, 800 mg (4.15 mmol) copper (I) iodide and 630 μl (7.79 mmol) pyridine in 8.0 ml of N,N-dimethylacetamide. The flask was sealed and was heated to 70° C. during stirring for a period of 16 hours. The reaction mixture was allowed to cool to room temperature and was then added to 100 ml of water. The suspension was adjusted to pH 13 with sodium hydroxide solution and was stirred for 15 minutes at room temperature. The suspension was filtered and the filtrate was adjusted to pH 4.5 with concentrated aqueous HCl. Filtration of the resulting slurry provided 451 mg (41%) of 2-cyclopropylamino-4,5-difluorobenzoic acid; m.p.: 175°-176° C.

Workup

customTo a 10 ml resealable pressure reaction flask
customequipped with a magnetic stirrer
customThe flask was sealed
temperatureto cool to room temperature
stirringwas stirred for 15 minutes at room temperature
filtrationThe suspension was filtered
filtrationFiltration of the resulting slurry

Sources & evidence

ORD record: ord-40065f8587374d72922736b1916a88c5
Source dataset: uspto-grants-1991_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05064958

Linked notes

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