3-(Dimethylamino)-1-propanol → 3-Dimethylaminopropyl 4-benzyloxy-5,7-dichloroquinoline-2-carboxylate

HRID 326656Notes

Reaction equation

HRID 326656 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.[CH3:24][N:25]([CH3:30])[CH2:26][CH2:27][CH2:28]O>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][CH2:28][CH2:27][CH2:26][N:25]([CH3:30])[CH3:24])=[O:22])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 766463-(Dimethylamino)-1-propanolHCID 214789594-Benzyloxy-5,7-dichloroquinoline-2-carboxylic acid

Product 1

HCID 197351613-Dimethylaminopropyl 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 3-dimethylamino- 1-propanol (1.1 ml) as described in Example 33c gave 3-dimethylaminopropyl 4-benzyloxy-5,7-dichloroquinoline-2-carboxylate (0.52 g). δ (360 MHz, DMSO-d6) 1.93 (2H, m, CO2CH2CH2), 2.20 (6H, s, (CH3)2), 2.44 (2H, t, CH2N), 4.40 (2H, t, CO2CH2), 5.50 (2H s, OCH2), 7.34 (3H, m, m,p-ArH), 7.58 (2H, d, 2 ArH), 7.72 (1H, s, 3-H), 7.88 (1H, d, 6-H) and 8.14 (1H, d, 8-H).

Sources & evidence

ORD record
ord-0524cc461a644acf911ed95c2482114d
Source dataset
uspto-grants-1993_12
Patent number
US05270309

Reaction notes

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