Hydrochloric Acid → HCID 57969098, compound

HRID 1664353Notes

Reaction equation

HRID 1664353 reaction equation
[Cl:1][C:2]1[C:3]([O:13][C:14]2[CH:23]=[CH:22][C:17]3[B:18]([OH:21])[O:19][CH2:20][C:16]=3[CH:15]=2)=[N:4][CH:5]=[C:6]([CH:12]=1)[C:7]([O:9]CC)=[O:8].[OH-].[Na+].Cl.CCOC(C)=O>CO.CCCCCC>[Cl:1][C:2]1[C:3]([O:13][C:14]2[CH:23]=[CH:22][C:17]3[B:18]([OH:21])[O:19][CH2:20][C:16]=3[CH:15]=2)=[N:4][CH:5]=[C:6]([CH:12]=1)[C:7]([OH:9])=[O:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 57969177HCID 57969177, compound

Product 1

HCID 57969098HCID 57969098, compoundYield 92.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8058HexaneSolvent

Procedure

Hydrolysis of ethyl 5-chloro-6-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yloxy)nicotinate (0.9 g, 2.7 mmol) with 1N NaOH (11 mL) in MeOH (50 mL) overnight at r.t. followed by acidification with 6N HCl, work-up and recrystallization from EtOAc and hexane afforded off-white solid of the title carboxylic acid compound (0.76 g, 2.49 mmol, yield 92%).

Sources & evidence

ORD record
ord-f33a5ebdb40d4927b7cdf2088b12b686
Source dataset
uspto-grants-2011_10
Patent number
US08039450B2

Reaction notes

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