Hydrochloric Acid → N1-(2-(adamantan-1-yl)ethyl)-2-fluorobenzene-1,4-diamine

HRID 56211Notes

Reaction equation

HRID 56211 reaction equation
O.Cl.[C:3]12([CH2:13][CH2:14][NH:15][C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][C:17]=3[F:25])[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2>CO.[Fe]>[C:3]12([CH2:13][CH2:14][NH:15][C:16]3[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][C:17]=3[F:25])[CH2:4][CH:5]3[CH2:11][CH:9]([CH2:8][CH:7]([CH2:6]3)[CH2:12]1)[CH2:10]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 90023098N-(2-(adamantan-1-yl)ethyl)-2-fluoro-4-nitroaniline

Product 1

HCID 131736912N1-(2-(adamantan-1-yl)ethyl)-2-fluorobenzene-1,4-diamineYield 84.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst2×HCID 887MethanolSolvent

Procedure

To a mixture of water (50 mL) and iron powder (0.88 g, 15.8 mmol) at 65° C. was added concentrated hydrochloric acid (1 mL) dropwise and the mixture was stirred for 15 min. The aqueous layer of the mixture was poured out, and a solution of N-(2-(adamantan-1-yl)ethyl)-2-fluoro-4-nitroaniline (0.5 g, 1.57 mmol) in MeOH (50 mL) was added to the above processed iron powder. The mixture was further stirred at 65° C. for 30 min. The mixture was then cooled to rt and filtered. The filtrate was concentrated and the residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=4:1) to give the title compound as a white solid (382 mg, 84%).

Workup

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

Sources & evidence

ORD record
ord-5f30e95c613f4b7c924b41670bd71fee
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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