Sodium Hydroxide → 4-[2-(4-Chloro-phenyl)-ethyl]-3-methyl-1H-pyrrole-2-carboxylic acid

HRID 1434792Notes

Reaction equation

[OH-].[Na+].C([O:5][C:6]([C:8]1[NH:9][CH:10]=[C:11]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[C:12]=1[CH3:13])=[O:7])C>O1CCOCC1.O>[Cl:22][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][CH2:14][C:11]2[C:12]([CH3:13])=[C:8]([C:6]([OH:7])=[O:5])[NH:9][CH:10]=2)=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Freshly prepared aq. NaOH (1M in H2O, 10 equivalents) was added at room temperature to a stirred solution of 86 (1 equivalent) in a mixture of 1,4-dioxane and H2O (v/v 3:1). The reaction was heated to 80° C. until the reaction was judged complete by TLC. The product was extracted with Et2O, then the aqueous layer was made acid (pH=1) with the dropwise addition of 10% aq. HCl. The solid was filtered off and washed with water. The solid was dried under vacuum overnight to obtain 87. Yield: 66%. 1H-NMR (400 MHz, CD3OD): δ 2.19 (s, 3H), 2.69 (m, 2H), 2.78 (m, 2H), 6.58 (d, 1H), 7.11 (d, 2H), 7.22 (d, 2H) ppm. LC/MS: 100%, m/z=263. HPLC (200-400 nm): 95.93%

Workup

extractionThe product was extracted with Et2O
additionwith the dropwise addition of 10% aq. HCl
filtrationThe solid was filtered off
washwashed with water
customThe solid was dried under vacuum overnight

Sources & evidence

ORD record: ord-dda8ca4d0665490b98bef530841a195e
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07615572B2

Reaction notes

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