Ammonium Chloride → HCID 68640582, compound

HRID 1928763Notes

Reaction equation

HRID 1928763 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[C:8]([O:12][CH3:13])=[C:7]2[C:3]=1[CH2:4][CH2:5][CH:6]2[NH:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[C:20]([N+:25]([O-])=O)[CH:21]=2)[N:16]=1.[Cl-].[NH4+]>C(O)C.O.[Fe]>[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[C:8]([O:12][CH3:13])=[C:7]2[C:3]=1[CH2:4][CH2:5][CH:6]2[NH:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[C:20]([NH2:25])[CH:21]=2)[N:16]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 68633231HCID 68633231, compound

Product 1

HCID 68640582HCID 68640582, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Rac-(4,6-dichloro-7-methoxy-indan-1-yl)-(6-nitro-quinolin-2-yl)-amine (250 mg, 0.62 mmol) were taken up in a mixture of ethanol (5 mL) and water (2.5 mL). After the addition of ammonium chloride (17 mg, 0.31 mmol) and iron powder (173 mg, 3.1 mmol) the reaction mixture was heated tom reflux for 6 h. After cooling to ambient temperature the reaction mixture was filtered through Dicalit®, the filtrate was concentrated and the residue was subjected to column chromatography (silica gel, heptane ethyl acetate gradient 9:1→1:1). Rac-N2-(4,6-dichloro-7-methoxy-indan-1-yl)-quinoline-2,6-diamine was obtained as a yellow oil (0.11 g, 45%); MS: m/e=375.4 (M+H+).

Workup

  1. temperaturewas heated tom
  2. temperaturereflux for 6 h
  3. filtrationwas filtered through Dicalit®
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-904d9a2c98604dc4a45bcd8f27791b44
Source dataset
uspto-grants-2012_05
Patent number
US08183380B2

Reaction notes

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