Hydrochloric Acid → 4-(Tert-butyl)cinnamic acid

HRID 730263Notes

Reaction equation

C(N1C2C(=CC=C(N[C:14](=[O:27])/[CH:15]=[CH:16]/[C:17]3[CH:22]=[CH:21][C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:19][CH:18]=3)C=2)C(C)(C)C1)(=O)C.C(N1C2C(=CC=C([N+]([O-])=O)C=2)C(C)(C)C1)(=[O:32])C.O.O.[Sn](Cl)Cl.Cl>C(OCC)C>[C:23]([C:20]1[CH:19]=[CH:18][C:17](/[CH:16]=[CH:15]/[C:14]([OH:27])=[O:32])=[CH:22][CH:21]=1)([CH3:24])([CH3:25])[CH3:26]

Participants

Conditions

Temperature: 0 °C

Procedure

(2E)-N-(1-Acetyl-3,3-dimethylindolin-6-yl)-3-[4-(tert-butyl)phenyl]prop-2-enamide. To a solution of 1-acetyl-3,3-dimethyl-6-nitroindoline, Example 31(c), (110 mg, 0.47 mmol) in ethyl ether (3 mL), magnetically stirred in a round-bottomed flask at 0° C., was added tin (II) chloride dihydrate (0.67 g, 2.96 mmol, Aldrich) and cond HCl (0.3 mL). The reaction mixture was stirred at 0° C. for 10 min, allowed to warm to 25° C. then stirred at that temperature overnight. The reaction mixture was washed with 10 N NaOH (10 mL), extracted with EtOAc and concentrated in vacuo. Analogous to the procedure used to prepare Example 1, the crude product and 4-tert-butyl-trans-cinnamic acid (92 mg, 0.45 mmol, EMKA-Chemie) provided, after purification by silica gel chromatography (2:3 hexane:EtOAc), the title product. MP 121° C. MS (ESI, pos. ion) m/z: 391 (M+1).

Workup

temperatureto warm to 25° C.
stirringthen stirred at that temperature overnight
washThe reaction mixture was washed with 10 N NaOH (10 mL)
extractionextracted with EtOAc
concentrationconcentrated in vacuo
customto prepare Example 1

Sources & evidence

ORD record: ord-d51dae149bac4a3f8afed924d9869df3
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582657B2

Reaction notes

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