Ammonium Chloride → HCID 58677640, compound

HRID 1012664Notes

Reaction equation

HRID 1012664 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N+:15]([O-])=O)[CH:5]=[CH:4][C:3]=1[C:18]([C:20]1[CH:25]=[C:24]([O:26][CH2:27][CH:28]([OH:31])[CH2:29][OH:30])[CH:23]=[CH:22][C:21]=1[F:32])=[O:19].[NH4+].[Cl-]>CO.[Zn]>[NH2:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[NH:8][C:6]1[CH:5]=[CH:4][C:3]([C:18]([C:20]2[CH:25]=[C:24]([O:26][CH2:27][CH:28]([OH:31])[CH2:29][OH:30])[CH:23]=[CH:22][C:21]=2[F:32])=[O:19])=[C:2]([Cl:1])[CH:7]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 58677642HCID 58677642, compound

Product 1

HCID 58677640HCID 58677640, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

Compound 520 (37 mg, 0.08 mmol) was dissolved in MeOH (2 mL), NH4Cl (29 mg, 0.55 mmol) and Zn-dust (72 mg, 1.10 mmol) were added. Reflux for 0.5 h, allowed to cool to RT and filtered. Purified by flash chromatography using DCM:MeOH (v:v=95:5) as the eluent, affording the title compound. 13C NMR (CD3OD) δ 192.4, 156.5 (d), 156.2 (d), 153.1, 144.8, 136.3, 135.1, 129.9 (d), 128.4, 128.1, 127.1, 126.8, 120.8 (d), 119.6, 118.0 (d), 117.7, 116.5 (d), 115.8, 112.5, 71.7, 71.2, 64.0

Workup

  1. temperatureReflux for 0.5 h
  2. filtrationfiltered
  3. customPurified by flash chromatography

Sources & evidence

ORD record
ord-109fc0b474024d2d97dc8c0d62eb7c28
Source dataset
uspto-grants-2011_07
Patent number
US07977387B2

Reaction notes

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