Acetonitrile → HCID 178465566, compound

HRID 386674Notes

Reaction equation

HRID 386674 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:23]2[O:24][C:25]3[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][C:26]=3[C:27](=[O:30])[C:28]=2[OH:29])[CH:12]=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:36](#[N:38])[CH3:37]>>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:23]2[O:24][C:25]3[CH:34]=[CH:33][C:32]([NH:35][C:36](=[NH:38])[CH3:37])=[CH:31][C:26]=3[C:27](=[O:30])[C:28]=2[OH:29])[CH:12]=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 66845442HCID 66845442, compound

Product 1

HCID 178465566HCID 178465566, compoundYield 92%

Conditions

Temperature
0 °C

Procedure

2-(3,4-dibenzyloxyphenyl)-3-hydroxy-6-amino-4H-1-benzopyran-4-one (1.9 g; 3.78 mmol) was suspended in acetonitrile (40 mL) and cooled at 0° C. HCl was bubbled into the solution upon saturation. The reaction was then stirred for 5 days at r.t. Upon completion, H2O (20 mL) was added and the acetonitrile removed under vacuum. The precipitate was filtered off and dried to afford the titled compound as a bright yellow solid. Yield: 92%. TLC (9/1 Chloroform/Methanol) Rf: 0.2. 1H-NMR (d6-DMSO): 11.61 (br s, 1H); 9.62 (s, 1H); 8.65 (s, 1H); 8.01 (d, 1H), 7.90 (d, 2H); 7.78 (d, 1H); 7.35 (d, 2H); 7.65 (dt, 2H); 6.93 (d, 1H); 3.35 (s, 3H)

Workup

  1. customHCl was bubbled into the solution upon saturation
  2. additionUpon completion, H2O (20 mL) was added
  3. customthe acetonitrile removed under vacuum
  4. filtrationThe precipitate was filtered off
  5. customdried

Sources & evidence

ORD record
ord-5aece45f48cb4a16992420c717e914eb
Source dataset
uspto-grants-2013_02
Patent number
US08372866B2

Reaction notes

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