Nitrogen → HCID 131735641, compound

HRID 530186Notes

Reaction equation

HRID 530186 reaction equation
[N+:1]([C:4]1[CH2:10][C:9](=[N:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH:8]=[CH:7][C:5]=1[NH2:6])([O-])=O.N#N>C1COCC1.[Pd]>[NH2:1][C:4]1[CH2:10][C:9](=[N:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=2)[CH:8]=[CH:7][C:5]=1[NH2:6]

Participants

5

Reactant 2

HCID 947Nitrogen2×HCID 131735642HCID 131735642, compound

Product 1

HCID 131735641HCID 131735641, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

According to a procedure similar to that of Preparation example 1, intermediate 2-nitro-4-(N-parafluorobenzyl-imino)-aniline was obtained by using o-nitro paraphenylene diamine and parafluorobenzaldehyde as starting materials. 2-nitro-4-(N-parafluorobenzyl-imino)-aniline (2.61 g, 0.01 mol) was dissolved in THF (30 mL) and air therein was replace with N2. Then Pd—C (10%, 261 mg) was rapidly added and N2 therein was replaced with H2. The hydrogenation reaction was conducted overnight, and the resulting reaction solution was filtered and concentrated to produce a product of 2-amino-4-(N-parafluorobenzyl-imino)-aniline (2.3 g, 99.6%, colorless oil, instable, prone to be oxidized and deteriorated), which was rapidly used in nest step. 1H NMR (300 MHz, CDCl3): δ 7.32 (t, J=8.7 Hz, 2H), 7.02 (t, J=8.7 Hz, 2H), 6.58 (d, J=8.7 Hz, 1H), 6.01-6.08 (m, 2H), 4.22 (s, 2H).

Workup

  1. customThe hydrogenation reaction
  2. customthe resulting reaction solution
  3. filtrationwas filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4d7a7e89ad194a49bab010938965e7f4
Source dataset
uspto-grants-2016_05
Patent number
US09353048B2

Reaction notes

Loading…