Hydrochloric Acid → HCID 24855325, compound

HRID 1616732Notes

Reaction equation

HRID 1616732 reaction equation
N1CCCCC1.[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[CH:12]=O.C([CH2:22][C:23]([NH:25][C:26]1[C:27]([C:36]([OH:38])=[O:37])=[CH:28][C:29]2[C:34]([CH:35]=1)=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:24])(O)=O.Cl>C1(C)C=CC=CC=1>[CH3:7][O:8][C:9]1[CH:10]=[C:11](/[CH:12]=[CH:22]/[C:23]([NH:25][C:26]2[C:27]([C:36]([OH:38])=[O:37])=[CH:28][C:29]3[C:34]([CH:35]=2)=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:24])[CH:14]=[CH:15][C:16]=1[O:17][CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 8419VeratraldehydeHCID 59333885HCID 59333885, compound

Product 1

HCID 24855325HCID 24855325, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Piperidine (0.23 mL, 2.3 mmol) was added to a suspension of 3,4-dimethoxybenzaldehyde (0.38 g, 2.3 mmol) and 3-(2-carboxyacetamido)-2-naphthoic acid (0.56 g, 2.0 mmol) in toluene (5.0 mL) and treated according to Procedure 2, acidifying with 1 M HCl. (E)-3-[[3-(3,4-Dimethoxyphenyl)-1-oxo-2-propenyl]amino]-2-naphthoic acid (0.51 g, 66%) was obtained as a yellow crystalline solid; mp 212-213° C.; δH (400 MHz, DMSO-d6) 3.80 (s, 3H, OCH3), 3.84 (s, 3H, OCH3), 6.82 (d, J=15.6 Hz, 1H, CH═CHCO), 6.99 (d, =8.2 Hz, 1H, H5′), 7.25 (dd, 4,6=8.2, J2′,6′=2.0 Hz, 1H, H6′), 7.38 (d, J2′,6′=2.0 Hz, 1H, H2′), 7.49 (t, J6,7=J7,8=8.0 Hz, 1H, H7), 7.58 (d, J=15.6 Hz, 1H, CH═CHCO), 7.62 (t, J5,6=J6,7=8.0 Hz, 1H, H6), 7.89 (d, J7,8=8.0 Hz, 1H, H8), 8.03 (d, J5,6=8.0 Hz, H5), 8.71 (s, 1H, H1), 9.05 (s, 1H, H4), 11.30 (s, 1H, NH); δC (100 MHz, DMSO-d6) 55.6, 55.7, 110.4, 111.6, 117.1, 117.6, 120.1, 122.6, 125.6, 127.1, 127.3, 128.2, 129.1, 129.3, 133.1, 135.5, 136.3, 141.4, 149.0, 150.6, 164.2, 169.5; HRMS (ESI) Calculated for C22H19NO6 [M+H]+ 378.1336. found 378.1345; vmax 797, 1022, 1134, 1233, 1512, 1665, 1693, 3048 cm−1.

Workup

  1. additiontreated

Sources & evidence

ORD record
ord-451bfdc7797242f1889f032ab7d583dd
Source dataset
uspto-grants-2014_07
Patent number
US08765812B2

Reaction notes

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