Benzaldehyde → 2-{[(2E)-3-phenylprop-2-enoyl]amino}benzoic acid

HRID 1616727Notes

Reaction equation

HRID 1616727 reaction equation
N1CCCCC1.C(=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:15]([CH2:18][C:19]([NH:21][C:22]1[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=1[C:24]([OH:26])=[O:25])=[O:20])(O)=O.Cl>C1(C)C=CC=CC=1>[O:20]=[C:19]([NH:21][C:22]1[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=1[C:24]([OH:26])=[O:25])/[CH:18]=[CH:15]/[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 8082PiperidineHCID 4399222-(2-Carboxyacetamido)benzoic acid

Product 1

HCID 57175632-{[(2E)-3-phenylprop-2-enoyl]amino}benzoic acidYield 96.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Piperidine (0.42 mL, 4.2 mmol) was added to a suspension of benzaldehyde (0.43 mL, 4.2 mmol) and 2-[(carboxyacetyl)amino]benzoic acid (0.83 g, 3.7 mmol) in toluene (5.0 mL) and treated according to Procedure 2, acidifying with 1 M HCl. (E)-2-[(1-oxo-3-phenyl-2-propenyl)amino]benzoic acid (0.95 g, 96%) was obtained as a pale yellow crystalline solid; mp 188-189° C., lit. [23] 196-197° C.; δH (500 MHz, DMSO-d6) 6.88 (d, J=16.0 Hz, 1H, CH═CHCO), 7.18 (t, J3,4=J4,5=8.0, 1H, H4), 7.41-7.45 (m, 3H, H3′, H4′, H5′), 7.62 (td, J4,5=J5,6=8.0, J3,5=1.5 Hz, 1H, H5), 7.62 (d, J=16.0 Hz, 1H, CH═CHCO), 7.72-7.74 (m, 2H, H2′, H6′), 8.00 (dd, J3,4=8.0, J3,5=1.5 Hz, 1H, H3), 8.59 (d, J5,6=8.0 Hz, 1H, H6), 11.32 (s, 1H, NH).

Workup

  1. additiontreated

Sources & evidence

ORD record
ord-9332429406f24f12bc8fb1b432693999
Source dataset
uspto-grants-2014_07
Patent number
US08765812B2

Reaction notes

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