Sodium Hydroxide → HCID 66810784, compound

HRID 388812Notes

Reaction equation

HRID 388812 reaction equation
C[O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[C:5]=1[NH2:11].C[O:14][C:15](=O)[CH:16]([CH3:19])[CH2:17]O.[OH-].[Na+]>Cl>[OH:14][CH2:15][CH:16]([C:19]1[NH:10][C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([C:3]([OH:2])=[O:12])[C:5]=2[N:11]=1)[CH3:17]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 521128Methyl 3-hydroxy-2-methylpropanoateHCID 5718252,3-Diaminobenzoic acid methyl ester

Product 1

HCID 66810784HCID 66810784, compoundYield 25.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2,3-diaminobenzoic acid methyl ester (2.1 g, 14.1 mmol) in 4 M HCl (90 mL) was added 2-methyl-3-hydroxypropionic acid methyl ester (5 g, 42.3 mmol). The mixture was stirred at ˜90° C. for 24 h. It was neutralized by use of aqueous sodium hydroxide solution to pH ˜3, and concentrated to dryness. The residue was suspended in methanol, and filtered through a filter paper. After the filtrate was concentrated, the remaining solid residue was dissolved in water and washed with ethyl acetate. The aqueous solution was evaporated in vacuo yielding the title intermediate as a pale yellow oil (˜800 mg). The crude product was used in the next step without further purification. (m/z): [M+H]+ calcd for C11H12N2O3 221.09. found 221.3. 1H-NMR (CD3OD) δ (ppm) 8.1 (d, 1H), 7.9 (m, 1H), 7.6 (t, 1H), 3.8 (m, 2H), 3.6 (m, 1H), 1.4 (d, 3H).

Workup

  1. concentrationconcentrated to dryness
  2. filtrationfiltered through a filter paper
  3. concentrationAfter the filtrate was concentrated
  4. dissolutionthe remaining solid residue was dissolved in water
  5. washwashed with ethyl acetate
  6. customThe aqueous solution was evaporated in vacuo

Sources & evidence

ORD record
ord-d4441f15395949ad923ccdc5adfd3cef
Source dataset
uspto-grants-2013_02
Patent number
US08377964B2

Reaction notes

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