Phenol, 4-methoxy-2-nitro- → HCID 117699259, compound

HRID 1049710Notes

Reaction equation

HRID 1049710 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[NH:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:13][CH:12]=1.COC1C=CC(O)=C([N+]([O-])=O)C=1.[C:37](Cl)(=[O:42])[CH2:38][C:39](Cl)=[O:40].C(=O)([O-])O.[Na+]>O1CCCC1>[CH3:9][O:8][C:6]1[CH:5]=[CH:4][C:3]2[N:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[CH:13][CH:12]=3)[C:37](=[O:42])[CH2:38][C:39](=[O:40])[NH:1][C:2]=2[CH:7]=1

Participants

6

Reactant 4

HCID 15285Phenol, 4-methoxy-2-nitro-HCID 74269Propanedioyl dichlorideHCID 516892Sodium BicarbonateHCID 131736038HCID 131736038, compound

Product 1

HCID 117699259HCID 117699259, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 4-(2-amino-4-methoxyphenylamino)phenylcarbamate (500 mg, 1.52 mmol) synthesized in the same manner as that of Example 1 by using 4-methoxy-2-nitrophenol as the starting material was dissolved in anhydrous tetrahydrofuran (30 mL), and the solution was added dropwise with malonyl chloride (0.178 mL, 1.82 mmol) on an ice bath. The mixture was stirred at room temperature for 16 hours. After completion of the reaction, the reaction mixture was added with saturated aqueous sodium hydrogencarbonate, the aqueous layer was extracted with chloroform, the organic layer was dried over sodium sulfate, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform/methanol=100/1) to give the title compound (230 mg, yield 38%).

Workup

  1. customAfter completion of the reaction
  2. extractionthe aqueous layer was extracted with chloroform
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol=100/1)

Sources & evidence

ORD record
ord-8fd25235d7b7496aa7ba416bc18afb21
Source dataset
uspto-grants-2016_07
Patent number
US09382236B2

Reaction notes

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