Hydrogen Peroxide → HCID 58036796, compound

HRID 1952009Notes

Reaction equation

HRID 1952009 reaction equation
[C:1]1([P:7]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[C:12]3[C:17]=2[NH:16][CH:15]([C:18]2[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]=[CH:20][CH:19]=2)[CH:14]=[CH:13]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:34]O>C(Cl)Cl>[C:28]1([P:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:8]2[CH:9]=[CH:10][CH:11]=[C:12]3[C:17]=2[NH:16][CH:15]([C:18]2[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]=[CH:20][CH:19]=2)[CH:14]=[CH:13]3)=[O:34])[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 58036794HCID 58036794, compound

Product 1

HCID 58036796HCID 58036796, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the procedure described for the synthesis of compound 5,8-diphenylphosphino-2-naphthale-1-yl-1,2-dihydroquinoline (11) (8.8 g, 20 mmol) in CH2Cl2 (60 mL) was oxidised with H2O2 (4.15 mL, 30% w/w in H2O, 40 mmol) to give compound 12 (8.3 g) in 91% yield. 1H NMR (400.13 MHz, CDCl3) δ 8.00 (d, 1H, J=8.4 Hz, C5′—H), 7.83 (dd, 1H, J=7.6, 2.0 Hz, C8′—H), 7.7-7.6 (m, 3H, C2′—H/Ph-H), 7.6-7.5 (m, 3H, Ph-H), 7.5-7.4 (m, 5H, C6′/7′—H/Ph-H), 7.4-7.3 (m, 2H, Ph-H), 7.29 (d, 1H, J=8.0 Hz, C4′—H), 7.19 (t, 1H, J=8.0 Hz, C3′—H), 6.96 (d, 1H, J=7.2 Hz, C5—H), 6.64 (ddd, 1H, J=13.6, 7.6, 1.2 Hz, C7—H), 6.44 (td, 1H, J=7.2, 2.8 Hz, C6—H), 6.34 (dt, 1H, J=10.0, 1.6 Hz, C4—H), 6.32 (t, 1H, J=1.6 Hz, C2—H), 5.78 (dd, 1H, J=10.0, 4.0 Hz, C3—H) ppm; 13C NMR (100.61 MHz, CDCl3) δ 148.3, 148.2, 139.2, 132.9, 131.9 (d, J=11.1 Hz), 131.8 (d, J=12.1 Hz), 131.2 (d, J=10.1 Hz), 130.9 (d, J=9.1 Hz), 130.7, 129.8, 128.4, 127.8, 127.5 (d, J=12.1), 127.3 (d J=12.1), 126.6, 125.3, 124.7, 124.5, 123.8, 123.7, 123.4, 121.5, 121.5, 118.9, 114.2, 114.0, 108.9, 107.8, 52.6 ppm; 31P NMR (161.97 MHz, CDCl3) δ+35.2 ppm.

Sources & evidence

ORD record
ord-462cceaf324248e1a51d87051b6f09f2
Source dataset
uspto-grants-2013_03
Patent number
US08404843B2

Reaction notes

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