Bromoacetonitrile → HCID 68961432, compound

HRID 269392Notes

Reaction equation

HRID 269392 reaction equation
[C:1]1([C:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[O:9][C:8]=2[C:16]2[CH:25]=[CH:24][C:23]([O:26]C)=[C:22]3[C:17]=2[CH:18]=[CH:19][CH:20]=[N:21]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:28]1([C:34]2[C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=3[O:36][C:35]=2[C:43]2[CH:52]=[CH:51][C:50]([OH:53])=[C:49]3[C:44]=2[CH:45]=[CH:46][CH:47]=[N:48]3)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.Br[CH2:55][C:56]#[N:57]>>[C:1]1([C:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[O:9][C:8]=2[C:16]2[CH:25]=[CH:24][C:23]([OH:26])=[C:22]3[C:17]=2[CH:18]=[CH:19][CH:20]=[N:21]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1.[C:28]1([C:34]2[C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=3[O:36][C:35]=2[C:43]2[CH:52]=[CH:51][C:50]([O:53][CH2:55][C:56]#[N:57])=[C:49]3[C:44]=2[CH:45]=[CH:46][CH:47]=[N:48]3)[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 11534BromoacetonitrileHCID 68959490HCID 68959490, compoundHCID 68959602HCID 68959602, compound

Product 2

HCID 68959490HCID 68959490, compoundHCID 68961432HCID 68961432, compoundYield 74%

Procedure

5-(3-Phenyl-1-benzofuran-2-yl)-8-hydroxy-quinoline was prepared as a solid (0.185 g, 99%) from 5-(3-phenyl-1-benzofuran-2-yl)-8-methoxy-quinoline according to the procedure described in the first part of Step 4 of Example 2; Mass spectrum (+ESI, [M+H]+) m/z 338. Reaction of 5-(3-phenyl-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 (0.148 g, 74%). Mass spectrum (+ESI, [M+H]+) m/z 377. 1H NMR (400 MHz, DMSO-d6): δ 8.90-8.96 (m, 1H), 8.19 (d, 1H, J=8.1 Hz), 7.71-7.81 (m, 3H), 7.39-7.65 (m,4H), 7.25-7.39 (m, 5H), and 5.48 ppm (s, 2H).

Sources & evidence

ORD record
ord-2f4ca3186ac8459e826839e1e1647386
Source dataset
uspto-grants-2008_11
Patent number
US07446201B2

Reaction notes

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