Sodium Hydroxide → 1-(3-methyl-butyl)-4-nitro-1H-pyrrole-2-carboxylic acid

HRID 644801

Reaction equation

[CH2:1]([N:6]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[C:7]1[C:14]([O:16]CC)=[O:15])[CH2:2][CH:3]([CH3:5])[CH3:4].[OH-].[Na+]>C(O)C>[CH2:1]([N:6]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[C:7]1[C:14]([OH:16])=[O:15])[CH2:2][CH:3]([CH3:5])[CH3:4]

Participants

Conditions

Temperature: 0 °C

Procedure

Ethyl 1-isopentyl-4-nitro-1H-pyrrole-2-carboxylate (2.377 g, 9.329 mmol; see step (i) above) was suspended in ethanol (5 mL), then a solution of NaOH (955 mg dissolved in 20 mL of water) was added. The reaction mixture was reduced by half under reduced pressure at 50° C., and then the cooled solution was extracted with ether. The water layer was cooled to 0° C. then conc. HCl was added dropwise with vigorous stirring until pH 2. The white solid material was filtered off, washed with water, dried at 60° C. under reduced pressure for 2 h then left at room temperature overnight. The product was obtained as white solid (2.008 g, 95% yield), m.p. 154-157° C. [Lit.m.p. 154-156° C.].

Workup

customwas reduced by half under reduced pressure at 50° C.
extractionthe cooled solution was extracted with ether
additionconc. HCl was added dropwise
filtrationThe white solid material was filtered off
washwashed with water
customdried at 60° C. under reduced pressure for 2 h

Sources & evidence

ORD record: ord-fc969097f8e0408eb4811a120b98eae3
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700765B2

Linked notes

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