Acetic Acid → 2-Propylamino-4-(trifluoromethyl)benzoic acid

HRID 1042444Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1042444
[NH2:1][C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:15](O)(=O)[CH3:16].[C:19](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[CH2:19]([NH:1][C:2]1[CH:10]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])[CH2:15][CH3:16]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 678694-(Trifluoromethyl)anthranilic acidHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 668556182-Propylamino-4-(trifluoromethyl)benzoic acidAusbeute 18 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2-Amino-4-(trifluoromethyl)benzoic acid (714 mg, 3.48 mmol), propionylaldehyde (0.27 ml, 3.74 mmol), acetic acid (3.49 mmol) and sodium triacetoxyborohydride (1.12 g, 5.25 mmol) were added in THF (40 ml). The reaction mixture was stirred overnight. The reaction mixture was quenched by adding sat. NaHCO3 (50 ml). The aqueous mixture was extracted with CH2Cl2 (30 ml×3). A combined organic layer was dried over MgSO4, concentrated in vacuo, and purified with column chromatography to yield title compound (155 mg, 18%).

Aufarbeitung

  1. customThe reaction mixture was quenched
  2. additionby adding sat. NaHCO3 (50 ml)
  3. extractionThe aqueous mixture was extracted with CH2Cl2 (30 ml×3)
  4. dry with materialA combined organic layer was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. custompurified with column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-73d66d025b7d4bda9b0c4eccf9c31d86
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08557872B2

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