Hydrochloric Acid → 2-chloro-N1-(2-methyl-1-(naphthalen-2-yl)propan-2-yl)benzene-1,4-diamine

HRID 56223Notes

Reaction equation

HRID 56223 reaction equation
O.Cl.[Cl:3][C:4]1[CH:24]=[C:23]([N+:25]([O-])=O)[CH:22]=[CH:21][C:5]=1[NH:6][C:7]([CH3:20])([CH3:19])[CH2:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1>C1COCC1.[Fe]>[Cl:3][C:4]1[CH:24]=[C:23]([NH2:25])[CH:22]=[CH:21][C:5]=1[NH:6][C:7]([CH3:20])([CH3:19])[CH2:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 900236622-chloro-N-(2-methyl-1-(naphthalen-2-yl)propan-2-yl)-4-nitroaniline

Product 1

HCID 900317672-chloro-N1-(2-methyl-1-(naphthalen-2-yl)propan-2-yl)benzene-1,4-diamineYield 84.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of water (50 mL) and iron powder (3.78 g, 67.7 mmol) at 65° C. was added concentrated hydrochloric acid (1.0 mL) dropwise and the mixture was stirred for 15 min. The aqueous layer of the mixture was poured out and a solution of 2-chloro-N-(2-methyl-1-(naphthalen-2-yl)propan-2-yl)-4-nitroaniline (2.4 g, 6.76 mmol) in THF (50 mL) was added to the above processed iron powder. The mixture was stirred further at 65° C. for 30 min. The mixture was then cooled to rt and filtered, and the filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=8:1) to give the title compound as a white solid (1.86 g, 84%).

Workup

  1. additionThe aqueous layer of the mixture was poured out
  2. stirringThe mixture was stirred further at 65° C. for 30 min
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=8:1)

Sources & evidence

ORD record
ord-8c30b6c9e6334455bfa1c9ee0d185283
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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