Iodoethane → HCID 178474098, compound

HRID 1680531Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[CH2:10][CH2:11][CH2:12][C:13](=[N:17][OH:18])[C:14]=2[C:15]=1[OH:16])=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:25](I)[CH3:26]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[CH2:10][CH2:11][CH2:12][C:13](=[N:17][O:18][CH2:25][CH3:26])[C:14]=2[C:15]=1[OH:16])=[O:5])[CH3:2]

Participants

Conditions

Temperature: 95 °C

Procedure

4-Hydroxy-5-hydroxyimino-5,6,7,8-tetrahydroquinoline-3-carboxylic acid ethyl ester (3.75 g) was suspended in 100 ml of dimethylformamide and then dissolved therein by stirring the suspension on an oil bath at 95° C. Thereafter, 1.04 g of potassium carbonate and then 2.32 g of ethyl iodide were added thereto. The resulting reaction mixture was stirred for 4 hours. After the dimethylformamide was distilled off under reduced pressure, water and ethyl acetate were added to the residue. The organic layer was separated and then stripped of solvent to obtain a yield of 3.0 g of the desired compound. This compound melted at 89°-91° C. (uncorrected values). Its infrared absorption spectrum (KBr tablet) had absorption peaks at 3440, 3000, 2960, 1740, 1640, 1465, 1220, 1190, 1110, 1060, and 990 cm-1, and its n.m.r. spectrum (CDCl3, 60Mc, TMS) had signals at δ values of 1.38 (3H, t, J=6.75 Hz), 1.42 (3H, t, J=7.5 HZ), 1.7-2.2 (2H, m), 2.7-3.15 (4H , m), 4.25 (2H, q. J=6.75 Hz), 4.40 (2H, q, J=7.5 Hz), and 8.77 (1H, s).

Workup

dissolutiondissolved
customThe resulting reaction mixture
stirringwas stirred for 4 hours
distillationAfter the dimethylformamide was distilled off under reduced pressure, water and ethyl acetate
additionwere added to the residue
customThe organic layer was separated

Sources & evidence

ORD record: ord-d35a3f8d16a9474c83d062745f15b2c9
Source dataset: uspto-grants-1981_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04273932

Reaction notes

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