Bromoacetonitrile → HCID 68956615, compound

HRID 269390Notes

Reaction equation

HRID 269390 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[CH:19]=[CH:18][C:17]([O:20]C)=[C:16]2[C:11]=1[CH:12]=[CH:13][CH:14]=[N:15]2.[O:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[CH:24]=[C:23]1[C:31]1[CH:40]=[CH:39][C:38]([OH:41])=[C:37]2[C:32]=1[CH:33]=[CH:34][CH:35]=[N:36]2.Br[CH2:43][C:44]#[N:45]>>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[CH:19]=[CH:18][C:17]([OH:20])=[C:16]2[C:11]=1[CH:12]=[CH:13][CH:14]=[N:15]2.[O:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[CH:24]=[C:23]1[C:31]1[CH:40]=[CH:39][C:38]([O:41][CH2:43][C:44]#[N:45])=[C:37]2[C:32]=1[CH:33]=[CH:34][CH:35]=[N:36]2

Participants

5

Reactant 3

HCID 11534BromoacetonitrileHCID 68957324HCID 68957324, compoundHCID 68958235HCID 68958235, compound

Product 2

HCID 68956615HCID 68956615, compoundYield 34%HCID 68957324HCID 68957324, compound

Procedure

5-(1-Benzofuran-2-yl)-8-hydroxy-quinoline was prepared as a solid (0.264 g, 99%) from 5-(1-benzofuran-2-yl)-8-methoxy-quinoline following the procedure described in the first part of Step 4 of Example 2. Mass spectrum (+ESI, [M+H]+) m/z 262. Reaction of 5-(1-benzofuran-2-yl)-8-hydroxy-quinoline with bromoacetonitrile according to the procedure described in Step 2 of Example 1 afforded the title compound as a solid (0.104 g, 34%). Mass spectrum (+ESI, [M+H]+) m/z 301. 1H NMR (500 MHz, DMSO-d6): δ 9.02 (d, 1H, J=1.4 Hz), 8.99 (d, 1H, J=9.3 Hz), 8.07 (d, 1H, J=8.3 Hz), 7.68-7.81 (m, 3H), 7.54 (d, 1H, J=8.3 Hz), 7.28-7.46 (m, 3H), and 5.51 ppm (s, 2H).

Sources & evidence

ORD record
ord-deec6d9f80c4462cb46ba4c0c1639920
Source dataset
uspto-grants-2008_11
Patent number
US07446201B2

Reaction notes

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