Hydrochloric Acid → 5-Amino-4-carbamoyl-2-methylbenzoic acid

HRID 906182Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 906182
[NH2:1][C:2]1[C:3]([C:13]([NH2:15])=[O:14])=[CH:4][C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].[OH-].[Na+].Cl>CO>[NH2:1][C:2]1[C:3]([C:13](=[O:14])[NH2:15])=[CH:4][C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67403771Methyl 5-amino-4-(aminocarbonyl)-2-methylbenzoate

Produkt 1

HCID 577483955-Amino-4-carbamoyl-2-methylbenzoic acidAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Methyl 5-amino-4-(aminocarbonyl)-2-methylbenzoate (108 mg, 0.52 mmol) was dissolved in methanol (1.5 mL) and was treated with 1 M sodium hydroxide (1.5 mL, 1.5 mmol) for 1 h. The reaction mixture was concentrated to afford an aqueous residue that was acidified with 1N hydrochloric acid to pH ˜3. The precipitate was collected by filtration, washed with water, and dried in vacuo to afford 5-amino-4-carbamoyl-2-methylbenzoic acid (60.8 mg, 0.31 mmol, 61% yield). 1H NMR (400 MHz, d6-DMSO): δ 12.95 (br s, 1H), 7.99 (br s, 1H), 7.52 (s, 1H), 7.42 (br s, 1H), 7.35 (s, 1H), 4.75 (br s, 2H), 2.33 (s, 3H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. customto afford an aqueous residue that
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water
  5. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5c6fbb80b9994bbb8fdb393f6b0ab162
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08012956B2

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