2-Diisopropylaminoethanol → 2-Diisopropylaminoethyl 4-benzyloxy-5,7-dichloroquinoline-2-carboxylate

HRID 326658

Reaction equation

HRID 326658 reaction equation
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([Cl:20])=[CH:16][C:17]=2[Cl:19])[N:12]=[C:11]([C:21]([OH:23])=[O:22])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:24]([N:27]([CH:31]([CH3:33])[CH3:32])[CH2:28][CH2:29]O)([CH3:26])[CH3:25]>S(Cl)(Cl)=O>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([Cl:20])=[CH:16][C:17]=2[Cl:19])[N:12]=[C:11]([C:21]([O:23][CH2:29][CH2:28][N:27]([CH:31]([CH3:33])[CH3:32])[CH:24]([CH3:26])[CH3:25])=[O:22])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 73132-DiisopropylaminoethanolHCID 214789594-Benzyloxy-5,7-dichloroquinoline-2-carboxylic acid

Product 1

HCID 197352282-Diisopropylaminoethyl 4-benzyloxy-5,7-dichloroquinoline-2-carboxylate

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

Treatment of 4-benzyloxy-5,7-dichloroquinoline-2-carboxylic acid (1 g, Example 33b) with thionyl chloride (10 ml) followed by 2-(diisopropylamino)ethanol (1.63 ml) as described in Example 33c gave 2-diisopropylaminoethyl 4-benzyloxy-5,7-dichloroquinoline-2-carboxylate (0.85 g). δ (360 MHz, DMSO-d6) 0.98 (12H, 2d, CH3), 2.77 (2H, t, CH2N), 3.01 (2H, m, C-H), 4.27 (2H, t, CO2CH2), 5.49 (2H, s, OCH2), 7.38 (1H, d, p-ArH), 7.44 (2H, t, m-ArH), 7.58 (2H, d, o-ArH), 7.72 (1H, s, 3-H), 7.81 (1H, d, 6-H) and 8.21 (1H, d, 8-H).

Sources & evidence

ORD record
ord-15220a0d4a9c4912a092b0fabf469269
Source dataset
uspto-grants-1993_12
Patent number
US05270309

Linked notes

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