Hydrochloric Acid → HCID 67410593, compound

HRID 709898Notes

Reaction equation

HRID 709898 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[C:14]([C:19]3([CH3:26])[NH:23]C(=O)N[C:20]3=[O:25])[CH:15]=[N:16]2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].CC[OH:29].[OH-].[Na+].Cl>O>[NH2:23][C:19]([C:14]1[CH:15]=[N:16][C:17]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([O:8][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[CH:18]=2)([CH3:26])[C:20]([OH:25])=[O:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 67407488HCID 67407488, compound

Product 1

HCID 67410593HCID 67410593, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 5-(7-(heptyloxy)quinolin-3-yl)-5-methylimidazolidine-2,4-dione (1 g, 2.8 mmol), EtOH (2 mL), H2O (4 mL), and NaOH (2.24 g, 56 mmol, 20 eq.) was stirred for 4 day at 110° C. Then, to the reaction mixture was added HCl (40%) to adjust to pH=5 and then the desired compound was generated as yellow solid (740 mg, yield 80%), without further purification for next step. ESI-MS: 331 (M+H)+. 1H NMR (300 MHz, CD3OD) δ: 0.81-0.83 (t, 3H), 1.06-1.09 (t, 3H), 1.18-1.33 (m, 8H), 1.41-1.45 (m, 2H), 1.75-1.78 (m, 2H), 1.96 (s, 3H), 3.48-3.53 (m, 2H), 4.04 (m, 2H), 7.18-7.24 (m, 2H), 7.79-7.81 (d, 1H), 8.39 (s, 1H), 8.89 (s, 1H).

Sources & evidence

ORD record
ord-bcc0ddbfbf8440f497ee23a318fd1cde
Source dataset
uspto-grants-2015_11
Patent number
US09181191B2

Reaction notes

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