Hydrochloric Acid → HCID 24855324, compound

HRID 1616778Notes

Reaction equation

HRID 1616778 reaction equation
N1CCCCC1.[CH3:7][O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][C:10]=1[O:17][CH2:18][CH2:19][C:20]#[C:21][CH2:22][CH3:23].C([CH2:27][C:28]([NH:30][C:31]1[CH:39]=[CH:38][CH:37]=[CH:36][C:32]=1[C:33]([OH:35])=[O:34])=[O:29])(O)=O.Cl>C1(C)C=CC=CC=1>[CH2:18]([O:17][C:10]1[CH:11]=[C:12](/[CH:13]=[CH:27]/[C:28]([NH:30][C:31]2[CH:39]=[CH:38][CH:37]=[CH:36][C:32]=2[C:33]([OH:35])=[O:34])=[O:29])[CH:15]=[CH:16][C:9]=1[O:8][CH3:7])[CH2:19][C:20]#[C:21][CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 4399222-(2-Carboxyacetamido)benzoic acidHCID 59333888HCID 59333888, compound

Product 1

HCID 24855324HCID 24855324, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Piperidine (0.21 mL, 2.2 mmol) was added to a suspension of 4-methoxy-3-(hex-3-ynyloxy)benzaldehyde (0.50 g, 2.2 mmol) and 2-[(carboxyacetyl)amino]benzoic acid (0.44 g, 2.0 mmol) in toluene (5 mL) and treated according to Procedure 2, acidifying with 1 M HCl. The crude product was recrystallised from EtOH providing (E)-2-[[3-(3-(hex-3-ynyloxy)-4-methoxyphenyl)-1-oxo-2-propenyl]amino]benzoic acid (0.58 g, 75%) as a yellow crystalline solid; mp 163-165° C.; δH (400 MHz, DMSO-d6) 1.05 (t, J=7.6 Hz, 3H, CH3), 2.15 (q, J=7.6 Hz, 2H, CH3CH2), 2.62 (t, J=7.6 Hz, 1H, OCH2CH2C), 3.80 (s, 3H, OCH3), 4.09 (t, J=7.6 Hz, 2H, OCH2), 6.80 (d, J=15.6 Hz, 1H, CH═CHCO), 6.99 (d, J5′,6′=8.0 Hz, 1H, H5′), 7.16 (t, J3,4=J4,5=8.0 Hz, 1H, H4), 7.25 (d, J5′,6′=8.0 Hz, 1H, H6′), 7.40 (s, 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), 8.61 (d, J5,6=8.0 Hz, 1H, H6), 11.26 (s, 1H, NH), 13.58 (br s, 1H, CO2H); δC (100 MHz, DMSO-d6) 11.8, 14.0, 19.3, 55.6, 67.0, 76.2, 83.0, 111.9, 112.0, 116.6, 120.0, 120.3, 122.6, 123.0, 127.3, 131.1, 134.0, 141.0, 141.6, 147.9, 150.8, 164.2, 169.4; HRMS (ESI) calculated for C23H23NO5 [M+H]+ 394.1649. found 394.1648; vmax 755, 1253, 1510, 1604, 1657, 3238, 3524 cm−1.

Workup

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

Sources & evidence

ORD record
ord-5eb0b5df2de24a83a8835b6372a5e5b1
Source dataset
uspto-grants-2014_07
Patent number
US08765812B2

Reaction notes

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