Hydrochloric Acid → 3,5-Dichloro-2-hydroxy-4-[2-(4-methylpiperazin-1-yl)-ethoxy]benzoic acid methyl ester

HRID 1822606Notes

Reaction equation

HRID 1822606 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][OH:10])[CH2:4][CH2:3]1.[CH3:11][O:12][C:13](=[O:24])[C:14]1[CH:19]=[C:18]([Cl:20])[C:17](O)=[C:16]([Cl:22])[C:15]=1[OH:23].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl>C(Cl)(Cl)Cl>[CH3:11][O:12][C:13](=[O:24])[C:14]1[CH:19]=[C:18]([Cl:20])[C:17]([O:10][CH2:9][CH2:8][N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)=[C:16]([Cl:22])[C:15]=1[OH:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 2311841-(2-Hydroxyethyl)-4-methylpiperazineHCID 15489807Methyl 3,5-dichloro-2,4-dihydroxybenzoate

Product 1

HCID 538925843,5-Dichloro-2-hydroxy-4-[2-(4-methylpiperazin-1-yl)-ethoxy]benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2-(4-methylpiperazin-1-yl) ethanol (14.42 g) and 3,5-dichloro-2,4-dihydroxybenzoic acid methyl ester (52.15 g) in chloroform (400 ml) were added triphenylphosphine (28.85 g) and azodicarboxylic acid diisopropyl (21.7 ml) at room temperature, and the mixture was stirred for 16 hours, 1N Hydrochloric acid (300 ml) was added to the reaction mixture for extraction to give a crude product of the title compound. Step 4) 3,5-Dichloro-2-hydroxy-4-[2-(4-methylpiperazin-1-yl)ethoxy]-benzoic acid (VII)

Sources & evidence

ORD record
ord-0eafee68ac1d45dd8d917a72f88f747b
Source dataset
uspto-grants-2006_05
Patent number
USRE039088E1

Reaction notes

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