4-Nitroaniline → HCID 4763835, compound

HRID 918810Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[N+:12]([C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1)([O-:14])=[O:13]>>[CH3:8][O:7][C:5](=[O:6])[C:4]1[CH:9]=[CH:10][CH:11]=[C:2]([NH:19][C:18]2[CH:20]=[CH:21][C:15]([N+:12]([O-:14])=[O:13])=[CH:16][CH:17]=2)[CH:3]=1

Participants

Reactant 2

HCID 74754-Nitroaniline

HCID 12070Methyl 3-bromobenzoate

Product 1

HCID 4763835HCID 4763835, compound

Procedure

Reaction of methyl 3-bromobenzoate with 4-nitroaniline according to general procedure A provided methyl ester of Compound 5 as an orange solid (59% yield). 1H NMR (CDCl3, 500 MHz): δ=8.16 (d, J=9.1 Hz, 2H), 7.89 (s, 1H), 7.83 (d, J=7.6 Hz, 1H), 7.47 (t, J=7.8 Hz, 1H), 7.41 (m, 1H), 6.98 (d, J=9.1 Hz, 2H), 6.31 (s, 1H), 3.94 (s, 3H). 13C NMR (CDCl3, 125 MHz): δ=166.7, 149.7, 140.7, 140.3, 132.2, 130.1, 126.5, 125.9, 125.7, 122.6, 114.4, 52.6.

Sources & evidence

ORD record: ord-83d8bfd09f854f0e818da46a1060bc9f
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09271961B2

Reaction notes

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