2-Methoxy-5-nitroaniline → HCID 67303179, compound

HRID 1951479Notes

Reaction equation

HRID 1951479 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[NH2:12].[C:13]([N:20]1[CH2:25][CH2:24][C:23](=O)[CH2:22][CH2:21]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].S([O-])([O-])(=O)=O.[Na+].[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[NH:12][CH:23]1[CH2:24][CH2:25][N:20]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:21][CH2:22]1

Participants

6

Reactant 4

HCID 74472-Methoxy-5-nitroanilineHCID 24436Sodium SulfateHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 67303179HCID 67303179, compoundYield 143.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Added 2-methoxy-5-nitro phenylamine (8.0 grams, 47.61 mmol) to a round bottomed flask, followed by the addition of 1-boc-4-piperidone (28.42 grams, 142.83 mmol), sodium sulfate (67.6 grams, 476 mmol) and acetic acid (80 mL). The above reaction mass was stirred for 8 hours at ambient temperature. Then added sodium triacetoxyborohydride (30.28 grams, 142.83 mmol) at 20-25° C. in 5 minutes and stirred the reaction mass for further 3 hours. The reaction mass was quenched into water (100 mL) and basified to pH: 9 with 50% aqueous sodium hydroxide solution. The product was extracted with ethyl acetate (4×50 mL). Combined organic layer was washed with brine (100 mL), dried over sodium sulfate and concentrated to obtain oily product. The product was further purified by column chromatography, the eluent being ethyl acetate, n-hexane and triethylamine, to obtain 24.01 grams of pure product.

Workup

  1. customThe above reaction mass
  2. stirringstirred the reaction mass for further 3 hours
  3. customThe reaction mass was quenched into water (100 mL)
  4. extractionThe product was extracted with ethyl acetate (4×50 mL)
  5. washCombined organic layer was washed with brine (100 mL)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customto obtain oily product
  9. customThe product was further purified by column chromatography

Sources & evidence

ORD record
ord-1fac4a0f5b3d4ae7bb7a37df1dc71457
Source dataset
uspto-grants-2013_03
Patent number
US08404720B2

Reaction notes

Loading…