Ammonium Chloride → 3-Amino-7-chloro-2-[(N-methoxy-N-methylamino)carbonyl]indole

HRID 379913Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([N:13]([O:15][CH3:16])[CH3:14])=[O:12])=[C:7]2[N+:17]([O-])=O.[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:17][C:7]1[C:6]2[C:10](=[C:2]([Cl:1])[CH:3]=[CH:4][CH:5]=2)[NH:9][C:8]=1[C:11]([N:13]([O:15][CH3:16])[CH3:14])=[O:12]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 7-chloro-2-[(N-methoxy-N-methylamino)carbonyl]-3-nitroindole (step 2, 420 mg, 1.5 mmol) in ethanol-water (2:1, 30 ml) was added iron powder (168 mg, 3 mmol) and ammonium chloride (160 mg, 3 mmol). The mixture was heated at 50° C. for 2 h, and then cooled to room temperature. After filtration through a pad of Celite, the filtrate was concentrated. The residue was purified by flash column chromatography eluting with ethyl acetate/hexane (1:10˜1:1) to give 287 mg (75%) of the title compound.

Workup

temperaturecooled to room temperature
filtrationAfter filtration through a pad of Celite
concentrationthe filtrate was concentrated
customThe residue was purified by flash column chromatography
washeluting with ethyl acetate/hexane (1:10˜1:1)

Sources & evidence

ORD record: ord-67591670adc14876be2afc5eef5cf8e7
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06300363B1

Reaction notes

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