Water → HCID 1040007, compound

HRID 1887433Notes

Reaction equation

HRID 1887433 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].[N+:11]([C:14]1[CH:15]=[C:16]([CH:18]=[C:19]([O:21][C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)[CH:20]=1)[NH2:17])([O-:13])=[O:12].O>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH:17][C:16]1[CH:18]=[C:19]([O:21][C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)[CH:20]=[C:14]([N+:11]([O-:13])=[O:12])[CH:15]=1)=[O:6]

Participants

6

Reactant 3

HCID 962WaterHCID 69252Benzoyl chloride, 3-chloro-HCID 4084981HCID 4084981, compound

Product 1

HCID 1040007HCID 1040007, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

3-Chlorobenzoyl chloride (79 mg, 0.45 mmol, 1.05 eq), 4-dimethylaminopyridine (55 mg, 0.45 mmol, 1.05 eq) and 3-nitro-5-(pyridin-3-yloxy)aniline (0.1 g, 0.43 mmol, 1 eq) were dissolved in CH2Cl2 (5 mL) and stirred at rt for 18 h. Water was added and the organic layer separated, dried (MgSO4), filtered, and concentrated in vacuo to afford 140 mg (88%) of the title compound as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ 10.78 (s, 1H), 8.58 (t, J=1.9 Hz, 1H), 8.53 (d, J=2.8 Hz, 1H), 8.50 (dd, J=4.6, 1.0 Hz, 1H), 8.01 (t, J=1.8 Hz, 1H), 7.91-7.87 (m, 2H), 7.70-7.65 (m, 2H), 7.60-7.56 (m, 2H), 7.53 (dd, J=8.4, 4.7 Hz, 1H); ES-MS [M+1]+: 370.1.

Workup

  1. customthe organic layer separated
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c652d2062fb448afa3f6761ad52aedb8
Source dataset
uspto-grants-2013_08
Patent number
US08501757B2

Reaction notes

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