Sodium Hydroxide → HCID 57748612, compound

HRID 906175Notes

Reaction equation

HRID 906175 reaction equation
[NH2:1][C:2]([C:4]1[C:14]([NH:15][CH:16]([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:13][C:7]([C:8]([O:10]CC)=[O:9])=[C:6]([Cl:21])[CH:5]=1)=[O:3].[OH-].[Na+]>CO>[NH2:1][C:2]([C:4]1[C:14]([NH:15][CH:16]([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:13][C:7]([C:8]([OH:10])=[O:9])=[C:6]([Cl:21])[CH:5]=1)=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67404305HCID 67404305, compound

Product 1

HCID 57748612HCID 57748612, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 4-(aminocarbonyl)-2-chloro-5-(pentan-3-ylamino)benzoate (126.5 mg, 0.40 mmol) in methanol (2 mL) was added 2 N aqueous sodium hydroxide (400 uL, 0.80 mmol). The mixture was stirred 4.5 h at room temperature. After acidification with 1 N hydrochloric acid (800 uL), the volatile solvent were removed. An insoluble solid material was then isolated from the aqueous residue by filtration. The solid was dried to give 4-(aminocarbonyl)-2-chloro-5-(pentan-3-ylamino)benzoic acid (73 mg, 0.26 mmol, 64% yield). 1H NMR (400 MHz, CD3OD): 7.65 (s, 1H), 7.07 (s, 1H), 3.35-3.29 (m, 1H buried), 1.69-1.47 (m, 4H), 0.94 (t, 6H).

Workup

  1. customAfter acidification with 1 N hydrochloric acid (800 uL), the volatile solvent were removed
  2. customAn insoluble solid material was then isolated from the aqueous residue by filtration
  3. customThe solid was dried

Sources & evidence

ORD record
ord-aa2d61f10259408db9d5575495ca1d7e
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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