Sodium Hydroxide → HCID 54173782, compound

HRID 1729080Notes

Reaction equation

HRID 1729080 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([NH:11][C:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([O:22]C)=[O:21])=[CH:16][CH:15]=2)=[O:13])[CH:8]=[CH:9][CH:10]=1)[CH3:3].[OH-].[Na+]>CO>[CH3:3][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([NH:11][C:12]([C:14]2[CH:15]=[CH:16][C:17]([C:20]([OH:22])=[O:21])=[CH:18][CH:19]=2)=[O:13])[CH:8]=[CH:9][CH:10]=1)[CH3:1]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54326665HCID 54326665, compound2×

Product 1

HCID 54173782HCID 54173782, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ester (IX; R=Z=H) (5.30 g, 17 mmol) in MeOH (10 mL) was treated with one equivalent of NaOH (17.0 nil of 1.0 N aqueous solution), and the mixture was heated until the MeOH had boiled off, and for 1 h under reflux, then cooled and filtered. Exact neutralisation (with17.0 mL of 1.0 N aqueous HCl) followed by refrigeration yielded 4-[3-(N,N-dimethylaminomethyl) phenyl]carbamoylbenzene-carboxylic acid (X;R=Z=H) (4.73 g, 93%), mp (MeOH/EtOAc) 209°-210 ° C. 1H NMR (CD3SOCD3) 10.41 (s, 1 H, NH), 8.07 (d, J=7.0 Hz, 2 H, H-2', 6'), 8.02 (d, J=7.0 Hz, 2 H, H-3',5'), 7.82 (s, 1 H, H-2), 7.72(d, J=8.05 Hz, 1 H, H-4), 7.33 (U, J= 7.8 Hz, 1 H, H-5), 7.09 (d, J=7.6 H z, 1 H, H -6 ), 3.61 (s, 2 H, CH2), 2.32 (s, 6 H, N(CH3)2).Anal. (C17H18N2O3) C, H, N.

Workup

  1. temperaturefor 1 h under reflux
  2. temperaturecooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-cf6832559df9488e8b2fe9da8cf1d18c
Source dataset
uspto-grants-1994_07
Patent number
US05331004

Reaction notes

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