N,N-dimethyl-m-phenylenediamine → HCID 59442894, compound

HRID 2176957Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[N:5]([CH3:7])[CH3:6].[CH3:11][N:12]([CH3:20])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([NH2:19])[CH:14]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].C1(C)C=CC=CC=1>[CH3:6][N:5]([CH3:7])[C:4]1[CH:3]=[C:2]([NH:19][C:15]2[CH:16]=[CH:17][CH:18]=[C:13]([N:12]([CH3:20])[CH3:11])[CH:14]=2)[CH:10]=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Under dinitrogen atmosphere, 1 equivalent of 3-bromo-N,N-dimethylaniline (1 g), 1.5 equivalent of sodium tert-butylate (0.721 g), 0.1 equivalent of Pd(dba)2 (0.288 g), 0.12 equivalent of dppf (0.555 g) and 20 mL of toluene are introduced into a flask. The flask is fitted with a PTFE septum and 1.2 equivalent of N,N-dimethylbenzene-1,3-diamine (0,817 g) is added thereto using a syringe. The reaction medium is heated at 90° C. for 12 hours, thereafter is cooled to room temperature and concentrated under reduced pressure. The product is purified by flash chromatography using a gradient of 5% to 12% of ethyl acetate in hexane (Rf: 0.33) to give 0.963 g of the expected product with a yield of 75%.

Workup

additionis added
temperatureis cooled to room temperature
concentrationconcentrated under reduced pressure
customThe product is purified by flash chromatography

Sources & evidence

ORD record: ord-5c074a8ebb7641158a504e9f0f336cde
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067900B2

Reaction notes

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