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3-Pyridinecarboxaldehyde → 4-(3-Pyridylmethylamino)-2-phenylbenzoic acid acetic acid salt

HRID 2121169
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2121169
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=O)[CH:2]=1.Cl.[NH2:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[C:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:12]=1.[BH3-]C#N.[Na+]>C(O)(=O)C.CO>[C:15]([OH:17])(=[O:16])[CH3:14].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:10][C:11]2[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[C:13]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:12]=2)[CH:2]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 103713-PyridinecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 698924925-Amino-[1,1'-biphenyl]-2-carboxylic acid hydrochloride

Produkt 1

HCID 698936704-(3-Pyridylmethylamino)-2-phenylbenzoic acid acetic acid saltAusbeute 186,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic Acid
Lösungsmittel
HCID 887MethanolLösungsmittel

Versuchsvorschrift

3-Pyridinecarboxaldehyde (1.2 mL, 12.8 mmol) and 4-amino-2-phenylbenzoic acid hydrochloride (3.2 g, 12.8 mmol), prepared in Example 190A, were dissolved in 100 mL 1% acetic acid in methanol. After stirring for 10 minutes, NaBH3CN was added, and stirring was continued for 18 hours. The reaction was evaporated to dryness under reduced pressure and partitioned between ethyl acetate and water. The aqueous phase was extracted with ethyl acetate. The organic extracts were combined, washed with brine, and dried over Na2SO4 to give 4-(3-Pyridylmethylamino)-2-phenylbenzoic acid acetic acid salt (4.35 g, 90%) of the title compound. MS m/e 305 (M+H)+. 1H NMR (d6-DMSO, 300 MHz) δ 4.41 (s, 2H), 6.45 (d, J=3 Hz, 1H), 6.60 (m, 1H), 7.15-7.90 (m, 10H), 8.48 (m, 1H), 8.60 (m, 1H).

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for 18 hours
  3. customThe reaction was evaporated to dryness under reduced pressure
  4. custompartitioned between ethyl acetate and water
  5. extractionThe aqueous phase was extracted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over Na2SO4

Quellen und Nachweise

ORD-Eintrag
ord-649e3c7f17444ebf92ab17b16b1a94a7
Quelldatensatz
uspto-grants-2004_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06693123B2

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