Hydrochloric Acid → 4-Benzyloxy-5,7-dichloroquinoline-2-carboxylic acid

HRID 326651Notes

Reaction equation

HRID 326651 reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]2[C:7](=[CH:8][C:9]([Cl:24])=[CH:10][C:11]=2[Cl:23])[N:6]=1)=[O:4].[OH-].[Na+].Cl>C(O)C.O>[CH2:16]([O:15][C:13]1[C:12]2[C:7](=[CH:8][C:9]([Cl:24])=[CH:10][C:11]=2[Cl:23])[N:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:14]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19735155Methyl 4-benzyloxy-5,7-dichloroquinoline-2-carboxylate

Product 1

HCID 214789594-Benzyloxy-5,7-dichloroquinoline-2-carboxylic acidYield 82.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of methyl-4-benzyloxy-5,7-dichloroquinoline-2-carboxylate (1.2 g) in ethanol (20 ml) was added a solution of sodium hydroxide (0.53 g) in water (20 ml) and the mixture was stirred at room temperature for 1 h. Hydrochloric acid (11M) was added until pH2 and the resulting precipitate was filtered off, washed with water (20 ml), ethanol (10 ml), diethylether (5 ml) and dried to yield 4-benzyloxy-5,7-dichloroquinoline-2-carboxylic acid (0.95 g). δ (360 MHz, DMSO-d6), 5.49 (2H, s, CH2), 7.40 (3H, m, m,p-ArH), 7.58 (2H, d, o-ArH), 7.71 (1H, s, 3-H), 7.83 (1H, d, 6-H) and 8.81 (1H, d, 8-H).

Workup

  1. filtrationthe resulting precipitate was filtered off
  2. washwashed with water (20 ml), ethanol (10 ml), diethylether (5 ml)
  3. customdried

Sources & evidence

ORD record
ord-c0b1b13828fd49ae8fc43ff324c0b428
Source dataset
uspto-grants-1993_12
Patent number
US05270309

Reaction notes

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