Potassium Carbonate → HCID 22349296, compound

HRID 896353Notes

Reaction equation

HRID 896353 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1Cl)[C:7]#[N:8])([O-:3])=[O:2].[NH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18].C([O-])([O-])=O.[K+].[K+]>CC#N>[C:7]([C:6]1[CH:9]=[CH:10][C:11]([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18])=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)#[N:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 13655Benzonitrile, 4-chloro-3-nitro-HCID 258684-Amino-1-butanol2×

Product 1

HCID 22349296HCID 22349296, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of 3-nitro-4-chloro-benzonitrile (20.4 g, 112.2 mmol), and 4-aminobutanol (10 g, 112 mmol) and K2CO3 (30.9 g, 224 mmol) in CH3CN (100 ml) was stirred at 23° C. for 12 h. Starting material remains by TLC analysis. Additional 4-aminobutanol (2 g, 22 mmol) was added and stirring continued for 24 h. The mixture is filtered and concentrated. The residue is dissolved in EtOAc and washed with water. The extracts are dried over MgSO4 and concentrated to give 26 g (99%) of 4-(4-cyano-2-nitro-phenylamino)-butan-1-ol as an orange solid.

Workup

  1. stirringstirring
  2. waitcontinued for 24 h
  3. filtrationThe mixture is filtered
  4. concentrationconcentrated
  5. dissolutionThe residue is dissolved in EtOAc
  6. washwashed with water
  7. dry with materialThe extracts are dried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-91665a3cd9224a729c46b2aeba020f9b
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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