Potassium Hydroxide → HCID 58970765, compound

HRID 1163078Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=2[N+:25]([O-:27])=[O:26])C(=O)C(F)(F)F)=[CH:6][CH:5]=1.[OH-].[K+]>C(Cl)Cl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=2[N+:25]([O-:27])=[O:26])=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 38 °C

Procedure

A stirred solution of 4{[(4-methyl-2-nitrophenyl)(2,2,2-trifluoroacetyl)-amino]methyl}benzoic acid methyl ester (14.0 g, 35 mmol) in CH2Cl2, was treated with tetrabutylammonium bromide (1.13 g, 3.5 mmol) and 20% aq. KOH (100 mL). The reaction mixture was heated to 38° C. for 3 h and cooled to room temperature. The phases were separated, the aqueous phase was extracted with CH2Cl2. The combined extracts and organic phase were washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo to afford 4-[(4-methyl-2-nitrophenylamino)methyl]-benzoic acid methyl ester as an orange solid. Yield: 90%. 1H NMR (400 MHz, CDCl3): 8.37 (bs, 1H); 8.02 (m, 3H); 7.40 (d, J=8 Hz, 2H); 7.19 (d, J=8 Hz, 1H); 6.63(d, J=8 Hz, 1H); 4.60(d, J=8 Hz, 2H); 3.91(s,3H); 2.35 (s, 1H).

Workup

temperaturecooled to room temperature
customThe phases were separated
extractionthe aqueous phase was extracted with CH2Cl2
washThe combined extracts and organic phase were washed with brine
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-f128664f4c1e4c6a979b620e1b0092a5
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820825B2

Reaction notes

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