Acetic Acid → HCID 24855442, compound

HRID 1616782Notes

Reaction equation

HRID 1616782 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][CH2:23][CH2:24][CH3:25].C([CH2:29][C:30]([NH:32][C:33]1[CH:41]=[CH:40][CH:39]=[CH:38][C:34]=1[C:35]([OH:37])=[O:36])=[O:31])(O)=O.CC(O)=O>C1(C)C=CC=CC=1>[CH3:7][O:8][C:9]1[CH:16]=[CH:15][C:12](/[CH:13]=[CH:29]/[C:30]([NH:32][C:33]2[CH:41]=[CH:40][CH:39]=[CH:38][C:34]=2[C:35]([OH:37])=[O:36])=[O:31])=[CH:11][C:10]=1[O:17][CH2:18][CH2:19][C:20]#[C:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 4399222-(2-Carboxyacetamido)benzoic acidHCID 59333897HCID 59333897, compound

Product 1

HCID 24855442HCID 24855442, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Piperidine (190 μL, 1.9 mmol) was added to a suspension of 4-methoxy-3-(oct-3-ynyloxy)benzaldehyde (0.50 g, 1.9 mmol) and 2-[(carboxyacetyl)amino]benzoic acid (0.39 g, 1.7 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-(4-methoxy-3-(oct-3-ynyloxy)phenyl)-1-oxo-2-propenyl]amino]benzoic acid (0.60 g, 82%) as a colourless crystalline solid; mp 157-158° C.; δH (400 MHz, DMSO-d6) 0.85 (t, J=7.2 Hz, 3H, CH3), 1.32-1.42 (m, 4H, CH3CH2CH2), 2.14 (t, J=7.2 Hz, 2H, CH2), 2.62 (t, J=7.2 Hz, 2H, CH2CH2O), 3.80 (s, 3H, OCH3), 4.10 (t, J=7.2 Hz, 2H, OCH2), 6.80 (d, J=15.6 Hz, 1H, CH═CHCO), 7.00 (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), 7.61 (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), 11.27 (s, 1H, NH), 13.58 (br s, 1H, CO2H); δC (100 MHz, DMSO-d6) 13.4, 17.8, 19.3, 21.3, 30.5, 55.6, 67.1, 76.9, 81.5, 111.9, 112.1, 116.6, 120.0, 120.3, 122.6, 122.9, 127.3, 131.1, 134.0, 141.0, 141.5, 147.9, 150.8, 164.2, 169.4; HRMS (ESI) calculated for C25H27NO5 [M+H]+ 421.1962. found 421.1962; vmax 757, 1131, 1259, 1515, 1582, 1671, 2954, 3335 cm−1.

Workup

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

Sources & evidence

ORD record
ord-a39fdb2759bb4dcbb8f0895dbfd61e2c
Source dataset
uspto-grants-2014_07
Patent number
US08765812B2

Reaction notes

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