Benzylamine → Ethyl 1-benzyl-3-cyano-1H-pyrrole-2-carboxylate

HRID 1473178Notes

Reaction equation

C(/C(/[CH:11]=[CH:12]/[C:13](/[C:21]#[N:22])=[C:14](\O)/[C:15]([O:17][CH2:18][CH3:19])=[O:16])=C(/O)\C(OCC)=O)#N.[CH2:23]([NH2:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C)C=O.C(OCC)(=O)C>[CH2:23]([N:30]1[CH:11]=[CH:12][C:13]([C:21]#[N:22])=[C:14]1[C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 95 °C

Procedure

A solution of (2E,4E,6E)-diethyl 3,6-dicyano-2,7-dihydroxyocta-2,4,6-trienedioate (18 g, 58.8 mmol) in N,N-Dimethylformamide (DMF) (100 mL) and Ethyl acetate (100 mL), was treated with benzylamine (15.44 mL, 141 mmol) and the resultant was heated at 95° C. for 3 hours. The dark mixture was concentrated and purified on silica gel (0-70% ethyl acetate/hexanes) to afford ethyl 1-benzyl-3-cyano-1H-pyrrole-2-carboxylate (8.7 g, 34.1 mmol, 60% yield) as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.25-7.45 (m, 3H) 7.11-7.16 (m, 2H) 6.84-6.87 (m, 1H) 6.53-6.58 (m, 1H) 5.59 (s, 2H) 4.37 (q, J=7.04 Hz, 2H) 1.40 (t, J=7.13 Hz, 3H); LCMS (m/z) ES+=255 (M+1).

Workup

concentrationThe dark mixture was concentrated
custompurified on silica gel (0-70% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-dc9d26a4ef65439988f97555781a7ecc
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012642B2

Reaction notes

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