Sodium Hydroxide → 1-amino-1H-pyrrole-2-carboxylic acid allyl ester

Temperature

25 °C

1H-Pyrrole-2-carboxylic acid allyl ester (Example 1a, 11.73 g, 78.12 mmol) was dissolved in methyl tert-butyl ether (150 mL) and a solution of sodium hydroxide (37 g, 925 mmol) in water (150 mL) was added. Solid ammonium chloride (25.1 g, 469 mmol), trioctylmethylammonium chloride (“Aliquat® 336”, 1 mL) and 28% aqueous ammonium hydroxide solution (50 mL) were added to the biphasic mixture. Under vigorous stirring, a 6.15% aqueous bleach solution (“Chlorox”, 250 mL) was slowly added over a period of 45 min via addition funnel upon which the color of the solution turned orange. After stirring for 1.5 h at 25° C., mixture was poured into methyl tert-butyl ether (150 mL) and the layers were separated. The organic layer was washed with a solution of sodium thiosulfate (10 g) in water (200 mL) and the organic layer was dried over sodium sulfate and filtered. The solvent was removed in vacuo to afford the desired product, 1-amino-1H-pyrrole-2-carboxylic acid allyl ester (8.03 g, 48.32 mmol, 62% yield) as a brown oil.

1. customthe layers were separated
2. washThe organic layer was washed with a solution of sodium thiosulfate (10 g) in water (200 mL)
3. dry with materialthe organic layer was dried over sodium sulfate
4. filtrationfiltered
5. customThe solvent was removed in vacuo

ORD record

ord-d79b40f67f764491b618437a8c2f545a

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07582754B2