1-Pyrrolidineethanol → 2-(1-Pyrrolidinyl)ethyl 4-benzyloxy-5,7-dichloroquinoline-2-carboxylate

HRID 326654Notes

Reaction equation

HRID 326654 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.O[CH2:25][CH2:26][N:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1>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][CH2:25][CH2:26][N:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)=[O:22])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 762881-PyrrolidineethanolHCID 214789594-Benzyloxy-5,7-dichloroquinoline-2-carboxylic acid

Product 1

HCID 197351692-(1-Pyrrolidinyl)ethyl 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 1-(2-hydroxyethyl) pyrrolidine (0.43 ml) as described in Example 33c, gave 2-(1-pyrrolidinyl)ethyl 4-benzyloxy-5,7-dichloroquinoline-2-carboxylate (0.7 g). δ (360 MHz, DMSOd6) 1.70 (4H, bs, pyrrolidine-3,4-H), 2.60 (4H, bs, pyrrolidine-2.5-H), 2.88 (2H, t, CH2N), 4.48 (2H, t, CO2CH2), 5.50 (2H, s, OCH2), 7.38 (3H, m, m,p-ArH), 7.58 (2H, d, o-ArH), 7.71 (1H, s, 3-H), 7.86 (1H, d, 6-H) and 8.13 (1H, d, 8-H).

Sources & evidence

ORD record
ord-7acf5c5aa74b4eb8957af0c3c9308379
Source dataset
uspto-grants-1993_12
Patent number
US05270309

Reaction notes

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