Potassium Carbonate → 4-(3-Ethynylphenoxy)benzene-1,2-diamine

HRID 1283512Notes

Reaction equation

HRID 1283512 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+].[C:15]([C:17]1[CH:18]=[C:19]([CH:33]=[CH:34][CH:35]=1)[O:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[C:23]([N+:30]([O-])=O)[CH:22]=1)#[CH:16]>O.CO>[C:15]([C:17]1[CH:18]=[C:19]([CH:33]=[CH:34][CH:35]=1)[O:20][C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[C:23]([NH2:30])[CH:22]=1)#[CH:16]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 24489Sodium DithioniteHCID 203569524-(3-Ethynylphenoxy)-1,2-dinitrobenzene

Product 1

HCID 213262494-(3-Ethynylphenoxy)benzene-1,2-diamineYield 85%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a rapidly stirred solution containing 41 g (230 mmoles) of sodium hydrosulfite and 32 g (230 mmoles) of potassium carbonate dissolved in 250 ml of water was added dropwise a solution containing 6.7 g (23.4 mmoles) of 4-(3-ethynylphenoxy)-o-dinitrobenzene dissolved in 50 ml of methanol. The reaction mixture changed from black to white within several minutes after the addition. The white solution was evaporated in vacuo at 50°C to remove the methanol. The remaining aqueous solution was then extracted with several 50 ml portions of methylene chloride. The combined extracts were washed with one 50 ml portion of water, dried over molecular sieves and evaporated to dryness to yield 4.45 g (85%) of 4-(3-ethynylphenoxy)-o-phenylenediamine in the form of a colorless oil.

Workup

  1. additionwas added dropwise a solution
  2. customwhite within several minutes
  3. additionafter the addition
  4. customThe white solution was evaporated in vacuo at 50°C
  5. customto remove the methanol
  6. extractionThe remaining aqueous solution was then extracted with several 50 ml portions of methylene chloride
  7. washThe combined extracts were washed with one 50 ml portion of water
  8. customdried over molecular sieves
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-78463fdcf1f147ca93140cc48d044d8f
Source dataset
uspto-grants-1976_08
Patent number
US03975444

Reaction notes

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