Sodium Dithionite → 3-Amino-4-(2,5-dichlorophenoxy)benzonitrile

HRID 1946848Notes

Reaction equation

HRID 1946848 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:3]=1[O:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][C:6]=1[N+:13]([O-])=O.S(S([O-])=O)([O-])=O.[Na+].[Na+]>C1COCC1.O>[NH2:13][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:5]=1[O:4][C:3]1[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:2]=1[Cl:1])[C:9]#[N:10]

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 595489424-(2,5-Dichlorophenoxy)-3-nitrobenzonitrile

Product 1

HCID 435182193-Amino-4-(2,5-dichlorophenoxy)benzonitrileYield 103.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The coupled product 34 was reduced with sodium hydrosulfite ((49.76 g, 268.56 mmol) in a mixture of THF (200 mL) and water (100 mL). After the reaction was complete, THF was removed in vacuo. The product was precipitated out from the remaining reaction mixture, and was collected via vacuum filtration to yield compound 35 (12.961 g, 103.7% yield, 97.3% pure). 1H NMR (500 MHz, DMSO-d6): δ 7.64 (d, J=9 Hz, 1H), 7.31 (dd, J1=9 Hz, J2=2 Hz, 1H), 7.13 (d, J=2 Hz, 1H), 7.08 (d, J=2 Hz, 1H), 6.93 (dd, J1=8 Hz, J2=2 Hz, 1H), 6.74 (d, J=8 Hz, 1H), 5.63 (s, 2H).

Workup

  1. customTHF was removed in vacuo
  2. customThe product was precipitated out from the remaining reaction mixture
  3. filtrationwas collected via vacuum filtration

Sources & evidence

ORD record
ord-a93c0b4c1d0f40f3a7e155e3a649ee78
Source dataset
uspto-grants-2013_03
Patent number
US08399456B2

Reaction notes

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