Sodium Hydroxide → HCID 10730311, compound

HRID 327195Notes

Reaction equation

HRID 327195 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([S:12]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[C:8]([O:10][CH3:11])[CH:9]=1)([O-])=O.[OH-].[Na+]>C(O)C>[CH3:11][O:10][C:8]1[CH:9]=[C:4]([NH2:1])[CH:5]=[CH:6][C:7]=1[S:12]([C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)(=[O:13])=[O:14]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10661433HCID 10661433, compound

Product 1

HCID 10730311HCID 10730311, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 5-nitro-2-(4-pyridylsulfonyl)anisole (3.00 g, 10.2 mmol) and stannous chloride dehydrate (11.49 g, 51.0 mmol) in absolute ethanol (35 mL) was heated at reflux for 1 hour. The reaction mixture was poured into ice water, and the aqueous solution basified with 15% NaOH and extracted with ethyl acetate (2×200 mL). The combined organic portions were dried (MgSO4) and the solvent removed in vacuo to yield the title benzeneamine as a pale yellow solid (2.23 g, 83%); mp 150°-152° C. 1H--NMR (250 MHz, d6--DMSO): 3.62 (s, 3H, OCH3) 6.18 (d, 1H, J=1.8 Hz, aromatic) 6.24 (d, 1H, J=1.9 Hz, aromatic) 6.28 (s, 2H, NH2) 7.58 (d, 1H, J=8.8 Hz, aromatic) 7.70 (dd, 2H, J=4.5, 1.5 Hz, aromatic) 8.79 (dd, 2H, J=4.4, 1.6 Hz, aromatic). MS (CI, CH4): 265 (M+1).

Workup

  1. temperatureat reflux for 1 hour
  2. extractionextracted with ethyl acetate (2×200 mL)
  3. dry with materialThe combined organic portions were dried (MgSO4)
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-977b4170329c42789fe17b2ea59cb160
Source dataset
uspto-grants-1993_12
Patent number
US05272163

Reaction notes

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