Hydrochloric Acid → HCID 24855269, compound

HRID 1616755Notes

Reaction equation

HRID 1616755 reaction equation
N1CCCCC1.[CH:7]1([O:12][C:13]2[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][C:14]=2[O:21][CH3:22])[CH2:11][CH2:10][CH2:9][CH2:8]1.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.Cl>C1(C)C=CC=CC=1>[CH:7]1([O:12][C:13]2[CH:20]=[CH:19][C:16](/[CH:17]=[CH:26]/[C:27]([NH:29][C:30]3[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=3[C:32]([OH:34])=[O:33])=[O:28])=[CH:15][C:14]=2[O:21][CH3:22])[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 4399222-(2-Carboxyacetamido)benzoic acidHCID 31527214-Cyclopentyloxy-3-methoxy-benzaldehyde

Product 1

HCID 24855269HCID 24855269, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Piperidine (0.45 mL, 4.5 mmol) was added to a suspension of 4-cyclopentyloxy-3-methoxybenzaldehyde (1.0 g, 4.5 mmol) and 2-[(carboxyacetyl)amino]benzoic acid (0.92 g, 4.1 mmol) in toluene (5.0 mL) and treated according to Procedure 2, acidifying with 1 M HCl. The crude product was recrystallised from EtOH/water providing (E)-2-{[3-(4-cyclopentyloxy-3-methoxyphenyl)-1-oxo-2-propenyl]amino}benzoic acid (1.06 g, 67%) as a pale yellow crystalline solid; mp 96-98° C.; δH (400 MHz, DMSO-d6) 1.46 (m, 2H, CH2), 1.67-1.71 (m, 4H, CH2), 1.90 (m, 2H, CH2), 3.81 (s, 3H, OCH3), 4.82 (t, J=5.6 Hz, 1H, OCH), 6.76 (d, J=15.6 Hz, 1H, CH═CHCO), 6.94 (d, J5′,6′=8.4 Hz, 1H, H5′), 7.15 (t, J3,4=J4,5=8.0 Hz, 1H, H4), 7.19 (dd, J5′,6′=8.4, J5′,6′=1.6 Hz, 1H, H6′), 7.35 (d, J2′,6′=1.6 Hz, 1H, H2′), 7.54 (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), 13.59 (br s, 1H, CO2H); δC (100 MHz, DMSO-d6) 23.7, 32.3, 55.7, 79.5, 110.9, 114.0, 116.5, 119.7, 120.3, 122.5, 122.6, 127.0, 131.1, 134.0, 141.1, 141.7, 149.0, 149.6, 164.2, 169.5; HRMS (ESI) calculated for C22H23NO5 [M+Na]+ 404.1468. found 404.1468; vmax 747, 1261, 1506, 1584, 1659, 2964, 3524 cm−1.

Workup

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

Sources & evidence

ORD record
ord-08b9e3a6e2d245e2b90e49d9dc4db576
Source dataset
uspto-grants-2014_07
Patent number
US08765812B2

Reaction notes

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