tert-Butanol → Tert-butyl 4-aminonaphthalene-1-carboxylate

HRID 1884607Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1884607
Cl.[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]([OH:15])=[O:14])=[CH:5][CH:4]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[C:28](O)([CH3:31])([CH3:30])[CH3:29]>C(N(CC)CC)C.CCOC(C)=O>[C:28]([O:14][C:13]([C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]([NH2:2])=[CH:4][CH:5]=1)=[O:15])([CH3:31])([CH3:30])[CH3:29]

Komponenten

6

Edukt 3

HCID 6386tert-ButanolHCID 682631,1'-CarbonyldiimidazoleHCID 222621904-Amino-1-naphthalenecarboxylic acid hydrochloride

Produkt 1

HCID 20742840Tert-butyl 4-aminonaphthalene-1-carboxylateAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

3.6 g (16 mmol) of 4-Amino-naphthalene-1-carboxylic acid hydrochloride, (T. Nakayama et al, Chem. Pharm. Bull, 1984, 32, 3968-3980), was suspended in 44 mL of tert-butyl alcohol and 3.3 mL of triethylamine. To this was added 3.1 g (19 mmol) of carbonyldiimidazole. An exothermic reaction was noted, and the brown solution was stirred at room temperature for 12 h. After this time, the reaction was diluted with EtOAc, filtered through diatomaceous earth and concentrated in vacuo. Purification on silica gel, eluting with 20% EtOAc-hexanes provided 1.1 g of 4-amino-naphthalene-1-carboxylic acid tert-butyl ester as an off-white solid (29%).

Aufarbeitung

  1. customAn exothermic reaction
  2. filtrationfiltered through diatomaceous earth
  3. concentrationconcentrated in vacuo
  4. customPurification on silica gel
  5. washeluting with 20% EtOAc-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-774162e4cdbe4214b7297ca6019325db
Quelldatensatz
uspto-grants-2004_07
Patentnummer
US06765009B2

Notizen zur Reaktion

Wird geladen…