Acetic Acid → HCID 24855445, compound

HRID 1616788Notes

Reaction equation

HRID 1616788 reaction equation
N1CCCCC1.[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH:18]([CH2:21][CH3:22])[CH2:19][CH3:20])[CH:12]=O.C([CH2:26][C:27]([NH:29][C:30]1[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=1[C:32]([OH:34])=[O:33])=[O:28])(O)=O.CC(O)=O>C1(C)C=CC=CC=1>[CH3:7][O:8][C:9]1[CH:10]=[C:11](/[CH:12]=[CH:26]/[C:27]([NH:29][C:30]2[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=2[C:32]([OH:34])=[O:33])=[O:28])[CH:14]=[CH:15][C:16]=1[O:17][CH:18]([CH2:21][CH3:22])[CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 4399222-(2-Carboxyacetamido)benzoic acidHCID 59333851HCID 59333851, compound

Product 1

HCID 24855445HCID 24855445, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Piperidine (220 μL, 2.2 mmol) was added to a suspension of 3-methoxy-4-(pent-3-yloxy)benzaldehyde (0.50 g, 2.2 mmol) and 2-[(carboxyacetyl)amino]benzoic acid (0.46 g, 2.1 mmol) in toluene (5 mL) and treated according to Procedure 2, acidifying with 20% AcOH. The crude product was recrystallised from EtOH/water providing (E)-2-[[3-(3-methoxy-4-(pent-3-yloxy)phenyl)-1-oxo-2-propenyl]amino]benzoic acid (0.52 g, 66%) as a yellow crystalline solid; mp 82-85° C.; δH (400 MHz, DMSO-d6) 0.88 (t, J=7.2 Hz, 6H, CH3), 1.60 (p, J=7.2 Hz, 4H, CH2), 3.82 (s, 3H, OCH3), 4.25 (t, J=7.2 Hz, 1H, OCH), 6.76 (d, J=15.6 Hz, 1H, CH═CHCO), 6.98 (d, J5′,6′=8.0 Hz, 1H, H5′), 7.15 (t, J3,4=J4,5=8.0 Hz, 1H, H4), 7.20 (dd, J5′,6′=8.0, J2′,6′=1.6 Hz, 1H, H6′), 7.36 (d, J2′,6′=1.6 Hz, 1H, H2′), 7.55 (d, J=15.6 Hz, 1H, CH═CHCO), 7.60 (t, J4,5=J5,6=8.0 Hz, 1H, H5), 8.00 (d, J3,4=8.0 Hz, 1H, H3), 8.62 (d, J5,6=8.0 Hz, 1H, H6), 11.28 (s, 1H, NH), 13.58 (br s, 1H, CO2H); δC (100 MHz, DMSO-d6) 9.3, 25.5, 55.7, 80.1, 111.2, 114.5, 116.6, 119.8, 120.3, 122.5, 122.6, 127.1, 131.1, 134.0, 141.1, 141.6, 149.6, 149.9, 164.2, 169.5; HRMS (ESI) calculated for C22H25NO5 [M−H]− 382.1555. found 382.1649; vmax 749, 1139, 1259, 1505, 1584, 1650, 2934 cm−1.

Workup

  1. additiontreated
  2. customThe crude product was recrystallised from EtOH/water

Sources & evidence

ORD record
ord-d0bde685937849eb8d1236b1164bf52f
Source dataset
uspto-grants-2014_07
Patent number
US08765812B2

Reaction notes

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