Hydrochloric Acid → (R)-3-Methyl-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)butanoic acid

HRID 1161230Notes

Reaction equation

HRID 1161230 reaction equation
[CH3:1][CH:2]([CH3:22])[C@@H:3]([N:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[N+:18]([O-:20])=[O:19])[C:9]1=[O:21])[C:4]([O:6]C)=[O:5].[OH-].[Li+].C(O)(C)(C)C.O.Cl>>[CH3:1][CH:2]([CH3:22])[C@@H:3]([N:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[N+:18]([O-:20])=[O:19])[C:9]1=[O:21])[C:4]([OH:6])=[O:5]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 6386tert-ButanolHCID 59515729(R)-Methyl 3-methyl-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)butanoate

Product 1

HCID 59515700(R)-3-Methyl-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)butanoic acid

Procedure

(R)-Methyl 3-methyl-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)butanoate (0.6 g, 0.002 mol) was stirred with lithium hydroxide (0.09 g, 0.004 mol) in tert-butyl alcohol (4 mL, 0.04 mol) and water (2 mL, 0.1 mol) at 0° C. for 3 hours. 1 N HCl was added until pH<7 and then the reaction mixture was extracted with CH2Cl2 (40 mL×3). The organic layers were dried over MgSO4, filtered, purified via flash chromatography (12 g silica gel, 0-50% EtOAc/Hexane) to give a yellow oil. MS m/z 291.0 (M+H)+

Workup

  1. extractionthe reaction mixture was extracted with CH2Cl2 (40 mL×3)
  2. dry with materialThe organic layers were dried over MgSO4
  3. filtrationfiltered
  4. custompurified via flash chromatography (12 g silica gel, 0-50% EtOAc/Hexane)
  5. customto give a yellow oil

Sources & evidence

ORD record
ord-112699841a7549cda9887d15891b2df4
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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