4-Nitroaniline → 2,2,4,6,7-Pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-amine

HRID 2112234Notes

Reaction equation

[N+:1](C1C=CC(N)=CC=1)([O-])=O.N([O-])=O.[Na+].[CH3:15][C:16]1([CH3:35])[CH:20]([C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)[C:19]2[C:28]([CH3:34])=[CH:29][C:30]([CH3:33])=[C:31]([CH3:32])[C:18]=2[O:17]1>Cl>[CH3:15][C:16]1([CH3:35])[CH:20]([C:21]2[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=2)[C:19]2[C:28]([CH3:34])=[C:29]([NH2:1])[C:30]([CH3:33])=[C:31]([CH3:32])[C:18]=2[O:17]1

Participants

Conditions

Temperature: 2.5 °C

Procedure

4-Nitroaniline (0.16 g) was dissolved in 2N hydrochloric acid (3 mL) at 60° C., and then cooled to 0 to 5° C. To the resultant solution was added sodium nitrite (79 mg), and stirred for 15 minutes. To the mixture were added 2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran (0.27 g) and a solvent (3 mL), and stirred under a nitrogen atmosphere. After completion of the reaction, a sample was taken from the mixture and its composition was measured with HPLC (*1). Solvents, reaction conditions and results of measurement are shown in Table 1.

Workup

customAfter completion of the reaction
customSolvents, reaction conditions
customresults of measurement

Sources & evidence

ORD record: ord-f95855421e6543d7b432ac7c9805f259
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07521545B2

Reaction notes

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