Acetone → HCID 23433564, compound

HRID 1939550Notes

Reaction equation

HRID 1939550 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH3:9])[CH:3]=1.II.[CH3:12][C:13]([CH3:15])=O>>[Br:1][C:2]1[CH:8]=[C:7]2[C:5](=[C:4]([CH3:9])[CH:3]=1)[NH:6][CH2:15][CH:13]=[CH:12]2

Participants

4

Reactant 3

HCID 180AcetoneHCID 807IodineHCID 114234-Bromo-2-methylaniline

Product 1

HCID 23433564HCID 23433564, compound

Procedure

4-Bromo-2-methylaniline (5.58 g, 30 mmol) was treated with iodine (0.2 g, 0.9 mmol) and acetone (150 mL) in a sealed tube at 80° C. for 24 h to provide 6-bromo-1,2-dihydro-8-methylquinoline (Compound 85 of Scheme XXII) in 9 % yield as a yellow oil (0.70g). Most of the aniline (>80%) was recovered. A mixture of the 6-bromo-1,2-dihydro-8-methylquinoline (90 mg, 0.33 mmol), 3-nitrobenzeneboronic acid (167 mg, 1.0 mmol), Pd(PPh3)4 (24 mg, 0.02 mmol), K2CO3 (190 mg, 1.38 mmol) in toluene (7 mL) and water (1.5 mL) was heated at 70° C. for 16 h. Standard work-up followed by chromatography afforded 23 mg (23%) of Compound 292 as a yellow oil. Data for CompOund 292: IR (neat) 3412, 2966, 1602, 1530, 1348; 1H NMR (400 MHz, CDCl3) 8.38 (t, J=2.0, 1 H), 8.08 (dd, J=7.8 and 2.0, 1 H), 7.85 (d, J=7.8, 1 H), 7.52 (t, J=7.8, 1 H), 7.24 (d, J=11.7, 1 H), 7.21 (d, J=1.9, 1 H), 5.39 (s, 1 H), 3.72 (bs, 1 H), 2.18 (s, 3 H), 2.07 (s, 3 H), 1.34 (s, 6 H); 13C NMR (100 MHz, CDCl3) 148.9, 143.7 142.0, 132.2, 129.6, 128.8, 128.7, 128.6, 126.5, 121.3, 121.0, 120.7, 120.6, 120.3, 52.3, 31.9, 19.2, 17.3.

Sources & evidence

ORD record
ord-fcf7b80e882048569d8c667e3c0e6739
Source dataset
uspto-grants-1997_12
Patent number
US05696133

Reaction notes

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