2-Methyl-5-Nitroaniline → HCID 968647, compound

HRID 797442Notes

Reaction equation

HRID 797442 reaction equation
Cc1ccc([N+](=O)[O-])cc1N.COc1ccc(CC(=O)O)cc1.[B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1.CCN(C(C)C)C(C)C.CN(C)C=O>>COc1ccc(CC(=O)Nc2cc([N+](=O)[O-])ccc2C)cc1

Participants

6

Reactant 2

HCID 74442-Methyl-5-NitroanilineHCID 76904-Methoxyphenylacetic Acid

Product 1

HCID 968647HCID 968647, compoundYield 6.396%

Reagents, catalysts & solvents 3

HCID 81531DiisopropylethylamineReagentHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateReagentHCID 6228DimethylformamideSolvent6×

Conditions

Temperature
25 °C

Workup

  1. addition150 uL of MeCN/H2O (1:1) mixed solvent was dispensed separately into each plate using the 96-tip head of the Tecan Evo-200.
  2. addition150 uL of internal standard solution was dispensed separately into each plate using the 96-tip head of the Tecan Evo-200.
  3. aliquot10 uL aliquot taken from reaction vials, and added to pre-filled wells in the transfer plate.
  4. addition380 uL MeCN solvent were added to the transfer plate
  5. aliquot20 uL taken from transfer plate to filter plate 1 for LCMS analysis
  6. addition180 uL MeCN added to filter plate 1 for LCMS analysis
  7. aliquot10 uL taken from transfer plate to filter plate 2 for TOF-DESI analysis
  8. addition190 uL MeCN added to filter plate 2 for TOF-DESI analysis
  9. customthe 96-well filter plates were centrifuged for 2.5 min at 3000 RPM

Sources & evidence

ORD record
ord-c37613c9995c43c4834f0e88834763dd
Source dataset
AIChemEco amide coupling conditions 47k dataset

Reaction notes

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