Water → HCID 43518238, compound

HRID 1184376Notes

Reaction equation

HRID 1184376 reaction equation
[CH3:1][C:2]1[CH:19]=[CH:18][C:17]([CH3:20])=[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+].O.O1CCOCC1>C1COCC1>[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]([CH3:20])[CH:18]=[CH:19][C:2]=1[CH3:1])[C:9]#[N:10]

Participants

6

Reactant 4

HCID 962WaterHCID 24489Sodium DithioniteHCID 312751,4-DioxaneHCID 27815831HCID 27815831, compound

Product 1

HCID 43518238HCID 43518238, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The coupled product 30 (12.00 g, 44.73 mmol) was reduced with sodium hydrosulfite (30.47 g, 175.00 mmol) in a mixture of THF (75 mL), water (100 mL), and dioxane (45 mL). After the reaction is complete, volatile organic solvents were removed in vacuo and the precipitate in the remaining water was collected via vacuum filtration to afford compound 31 as a white solid (9.50 g, 89.0% yield, 99.5% pure). 1H NMR (500 MHz, DMSO-d6): δ 7.19 (d, J=8 Hz, 1H), 7.07 (d, J=2 Hz, 1H), 6.94 (d, J=8 Hz, 1H), 6.86 (dd, J1=8 Hz, J2=2 Hz, 1H), 6.74 (s, 1H), 6.45 (d, J=8 Hz, 1H), 5.52 (s, 2H), 2.23 (s, 3H), 2.08 (s, 3H).

Workup

  1. customvolatile organic solvents were removed in vacuo
  2. filtrationthe precipitate in the remaining water was collected via vacuum filtration

Sources & evidence

ORD record
ord-2a9126ef3c744c9a838e9ad8bee9eddc
Source dataset
uspto-grants-2014_03
Patent number
US08669247B2

Reaction notes

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