Iodine → HCID 23433564, compound

HRID 1604791Notes

Reaction equation

HRID 1604791 reaction equation
[N+](C1C=C([C:10]2[CH:11]=[C:12]3[C:17](=[C:18]([CH3:20])[CH:19]=2)[NH:16][C:15](C)(C)[CH:14]=[C:13]3C)C=CC=1)([O-])=O.[Br:24]C1C=CC(N)=C(C)C=1.II>CC(C)=O>[Br:24][C:10]1[CH:11]=[C:12]2[C:17](=[C:18]([CH3:20])[CH:19]=1)[NH:16][CH2:15][CH:14]=[CH:13]2

Participants

5

Reactant 3

HCID 807IodineHCID 114234-Bromo-2-methylanilineHCID 23433684HCID 23433684, compound2×

Product 1

HCID 23433564HCID 23433564, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1,2-Dihydro-6-(3-nitrophenyl)-2,2,4,8-tetramethylquinoline (Compound 292, structure 86 of Scheme XXII, where R1 =R3-5 =H, R2 =nitro) 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 (0.70 g). 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=117, 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, 319.9, 19.2, 17.3.

Sources & evidence

ORD record
ord-91267c8018c1465a83745fe8c958caf7
Source dataset
uspto-grants-1999_11
Patent number
US05994544

Reaction notes

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