Water → HCID 22461260, compound

HRID 1937622Notes

Reaction equation

[CH3:1][C:2]1([CH3:17])[CH2:10][C:9]2[NH:8][C:7](C(O)=O)=[C:6]([CH2:14][CH3:15])[C:5]=2[C:4](=[O:16])[CH2:3]1.O>C(O)(=O)C.Cl>[CH3:17][C:2]1([CH3:1])[CH2:10][C:9]2[NH:8][CH:7]=[C:6]([CH2:14][CH3:15])[C:5]=2[C:4](=[O:16])[CH2:3]1

Participants

Conditions

Temperature: 100 °C

Procedure

A suspension of 6,6-dimethyl-3-ethyl-4-oxo-4,5,6,7-tetrahydro- 1H-indole-2-carboxylic acid (2.5 g, 0.011 mol) in acetic acid (12 mL) and hydrochloric acid (10M; 0.64 mL) was heated at 100° C. for 45 min. After this time water (50 mL) was added, the cooling bath removed and the solution stirred at room temperature for 2 h. The precipitate was collected by filtration and the title pyrrole (1.76 g, 87%) isolated as a colourless solid. mp. 150° C.-152° C. C12H17NO requires: C, 75.35; H, 8.96; N, 7.32%. Found: C, 75.00; H, 8.88; N, 7.24%. 1H NMR (250 MHz, CDCl3) δ 1.10 (6H,s), 1.19 (3H,t,J=7.4 Hz), 2.32 (2H,s), 2.63 (2H,s), 2.75 (2H,d of q,J=7.4 and 1.0 Hz), 6.42 (1H,br s), 8.00 (1H,br s). MS (ES+) 192 (M+1).

Workup

customthe cooling bath removed
filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record: ord-69bb82b637bd4fdfb927ee33f1058995
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06395766B1

Reaction notes

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