Ammonium Chloride → HCID 58207676, compound

HRID 409985Notes

Reaction equation

[F:1][C:2]1[CH:30]=[C:29]([N+:31]([O-])=O)[CH:28]=[CH:27][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[N:19]=[CH:18][C:17]([CH2:20][N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)=[CH:16][CH:15]=3)[S:13][C:6]=12.[Cl-].[NH4+]>O.C(O)C.[Fe]>[F:1][C:2]1[CH:30]=[C:29]([CH:28]=[CH:27][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH:15]=[CH:16][C:17]([CH2:20][N:21]4[CH2:22][CH2:23][O:24][CH2:25][CH2:26]4)=[CH:18][N:19]=3)[S:13][C:6]=12)[NH2:31]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of the nitro compound 358 (432 mg, 0.926 mmol), iron powder (440 mg, 7.87 mmol), and ammonium chloride (42.6 mg, 0.796 mmol) in a mixture of water (3.00 mL) and ethanol (6 mL) was heated to 80° C. for 30 min. The reaction mixture was then filtered while hot through a pad of Celite. The filtrate was concentrated and the residue was purified using Biotage (eluent 0-20% EtOAc/MeOH, 10 g SNAP column) to afford the amine 359 (136 mg, 0.312 mmol, 33.6% yield) as a white solid. MS: 437 (MH)+.

Workup

filtrationThe reaction mixture was then filtered while hot through a pad of Celite
concentrationThe filtrate was concentrated
customthe residue was purified

Sources & evidence

ORD record: ord-6d55689cafb945998d090c93ce0a3fd8
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759522B2

Reaction notes

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