HCID 57961752, compound → HCID 57961539, compound

HRID 541799Notes

Reaction equation

HRID 541799 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:24]=[CH:25][CH:26]=1)[C:7]([NH:9][C:10]1[CH:11]=[C:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=[CH:14][CH:15]=1)=[O:8])([O-])=O>O.CO.C(O)(=O)C.[Fe]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:24]=[CH:25][CH:26]=1)[C:7]([NH:9][C:10]1[CH:11]=[C:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:20])[CH3:21])[CH:13]=[CH:14][CH:15]=1)=[O:8]

Participants

6

Reactant 1

HCID 57961752HCID 57961752, compound

Product 1

HCID 57961539HCID 57961539, compoundYield 87.3%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of tert-butyl {3-[(3-nitrobenzoyl)amino]phenyl}carbamate (2.00 g, 5.6 mmol) in water (4 mL), methanol (22 mL) and acetic acid (8.6 mL) was added iron (0.782 g, 14.0 mmol) powder in small quantities. When the addition was completed, the mixture was stirred in water bath for 3 h. The mixture was filtered, and the cake was washed with MeOH/EtOAc. The brown filtrate was concentrated and diluted with H2O, and the aqueous layer was extracted with EtOAc three times. The combined organic layers were dried, filtered and concentrated to give the desired product as an off-white powder (1.6 g, 87%). LCMS for C18H21N3O3 (M+H)+: m/z=328.1.

Workup

  1. additionWhen the addition
  2. filtrationThe mixture was filtered
  3. washthe cake was washed with MeOH/EtOAc
  4. concentrationThe brown filtrate was concentrated
  5. additiondiluted with H2O
  6. extractionthe aqueous layer was extracted with EtOAc three times
  7. customThe combined organic layers were dried
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-ebd1b5801f7f4f75b1f40557ea655cba
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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