4-[(2-hydroxyethyl)amino]-3-nitrobenzoic acid → HCID 4043952, compound

HRID 1907712Notes

Reaction equation

HRID 1907712 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][C:6]=1[N+:14]([O-])=O>CCOC(C)=O.CO.[Pd]>[NH2:14][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:5]=1[NH:4][CH2:3][CH2:2][OH:1])[C:9]([OH:11])=[O:10]

Participants

4

Reactant 1

HCID 29096234-[(2-hydroxyethyl)amino]-3-nitrobenzoic acid

Product 1

HCID 4043952HCID 4043952, compoundYield 101.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A solution of intermediate 156 (1.33 g, 5.9 mmol) in AcOEt/MeOH was stirred under H2 in the presence of 10% palladium on carbon for 18 h, filtered through Celite®, concentrated and then triturated with DCM to give compound 157 (1.18 g, >99% yield).

Workup

  1. filtrationfiltered through Celite®
  2. concentrationconcentrated
  3. customtriturated with DCM

Sources & evidence

ORD record
ord-591ae15508a246328e5d51b509857afc
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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