4-Bromoaniline → N-(4-Bromophenyl)-2-methoxy-5-nitro-benzoic acid amide

HRID 1846081Notes

Reaction equation

HRID 1846081 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:4]=1[C:5]([OH:7])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Br:39][C:40]1[CH:46]=[CH:45][C:43]([NH2:44])=[CH:42][CH:41]=1>C1COCC1>[Br:39][C:40]1[CH:46]=[CH:45][C:43]([NH:44][C:5](=[O:7])[C:4]2[CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=[CH:11][C:3]=2[O:2][CH3:1])=[CH:42][CH:41]=1

Participants

5

Reactant 3

HCID 78074-BromoanilineHCID 2841632-Methoxy-5-nitrobenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 9042746N-(4-Bromophenyl)-2-methoxy-5-nitro-benzoic acid amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-methoxy-5-nitro-benzoic acid (2.00 g, 10.1 mmol), HATU (3.86 g, 10.1 mmol), TEA (4.23 mL) and 100 mL THF was stirred for 30 min. Then 4-bromoaniline (1.75 g, 10.1 mmol) was added and the mixture was stirred for 3 days and concentrated. The crude material was dissolved in EtOAc and the organic phase was washed with satd. aq. NaHCO3. The precipitate was collected and again dissolved in EtOAc and washed with water and satd. NaHCO3. The organic phase was dried with Na2SO4, filtered and concentrated to furnish the subtitle compound. Yield: 930 mg (26%). MS [M+H]+=351 (Br-isotope pattern); TLC: Rf=0.94 (silica gel, DCM:EtOH 9:1).

Workup

  1. stirringthe mixture was stirred for 3 days
  2. concentrationconcentrated
  3. dissolutionThe crude material was dissolved in EtOAc
  4. washthe organic phase was washed with satd
  5. customThe precipitate was collected
  6. dissolutionagain dissolved in EtOAc
  7. washwashed with water
  8. dry with materialThe organic phase was dried with Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-c1132819fb484805ae8b60b97c717aab
Source dataset
uspto-grants-2015_02
Patent number
US08951999B2

Reaction notes

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