3-Aminophenol → HCID 69049437, compound

HRID 2383496Notes

Reaction equation

HRID 2383496 reaction equation
[H-].[Na+].[NH2:3][C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1.[C:11]([O:15][C:16](=[O:29])[N:17]([C:19]1[CH:24]=[C:23](Cl)[CH:22]=[CH:21][C:20]=1[N+:26]([O-:28])=[O:27])[CH3:18])([CH3:14])([CH3:13])[CH3:12]>CN(C)C=O>[C:11]([O:15][C:16](=[O:29])[N:17]([C:19]1[CH:24]=[C:23]([O:10][C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([NH2:3])[CH:5]=2)[CH:22]=[CH:21][C:20]=1[N+:26]([O-:28])=[O:27])[CH3:18])([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 115683-AminophenolHCID 24758Sodium hydrideHCID 15544598tert-butyl N-(5-chloro-2-nitrophenyl)-N-methylcarbamate

Product 1

HCID 69049437HCID 69049437, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 80 ml of anhydrous N,N-dimethylformamide suspension containing 2.18 g of sodium hydride (55 wt %) was added 5.45 g of 3-aminophenol, and the mixture was stirred at room temperature for 20 minutes. Subsequently, 14.3 g of N-(5-chloro-2-nitrophenyl)-N-methylcarbamic acid t-butyl ester (Japanese Patent Application (Kokai) No. Hei 11-193276) was added in small amounts, and the mixture was stirred at 100° C. for 6 hours. The reaction mixture was concentrated, followed by addition of water and neutralization using 3N hydrochloric acid and sodium bicarbonate powder. The insoluble product which deposited was filtered, washed with water, and then dried under reduced pressure to give the title compound (16.6 g, 92% yield).

Workup

  1. additionHei 11-193276) was added in small amounts
  2. stirringthe mixture was stirred at 100° C. for 6 hours
  3. concentrationThe reaction mixture was concentrated
  4. additionfollowed by addition of water and neutralization
  5. filtrationThe insoluble product which deposited was filtered
  6. washwashed with water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-3edebe7927f4466b83e3fc4fbaaeebf1
Source dataset
uspto-grants-2012_09
Patent number
US08263631B2

Reaction notes

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