Sodium Chloride → N1-(tert-Butoxycarbonyl)-4-fluoro-1,2-phenylenediamine

HRID 605857Notes

Reaction equation

HRID 605857 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[C:4]([N+:16]([O-])=O)[CH:3]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+].[Cl-].[Na+]>C1COCC1.O.CO>[NH2:16][C:4]1[CH:3]=[C:2]([F:1])[CH:7]=[CH:6][C:5]=1[NH:8][C:9](=[O:15])[O:10][C:11]([CH3:13])([CH3:12])[CH3:14]

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 59705030(4-Fluoro-2-nitro-phenyl)-carbamic acid tert-butyl ester

Product 1

HCID 24688763N1-(tert-Butoxycarbonyl)-4-fluoro-1,2-phenylenediamine

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4-fluoro-2-nitrophenylcarbamate (0.34 g) in THF (30 mL) was added a premixed solution of sodium hydrosulfite (2 g) and sodium bicarbonate (1 g) in water (50 mL). MeOH (10 mL) was also added to aid solution of the mixture, which was stirred at room temperature for 30 min, when sodium chloride was added to saturate the solution. The resulting mixture was extracted with EtOAc (2×). The combined organics were dried, filtered and evaporated to yield the titled compound (quant) that was used as such for the next step. 1H-NMR (300 MHz, CDCl3) δ 7.5 (dd, 1H), 6.6 (dd, 1H), 6.5 (m, 1H), 6.4 (br 1H), 4.7 (br 2H), 1.5 (s, 9H) ppm; MH+=227 (minor), 127 (-BOC), 171 (-tBu).

Workup

  1. concentrationto saturate the solution
  2. extractionThe resulting mixture was extracted with EtOAc (2×)
  3. customThe combined organics were dried
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-2e0756195efc449fb8bcc11edf9ee624
Source dataset
uspto-grants-2011_03
Patent number
US07915268B2

Reaction notes

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