N-bromobutanimide → HCID 89812883, compound

HRID 1481105Notes

Reaction equation

HRID 1481105 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([O:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1[Cl:25])[CH:10]=2)=[O:5])[CH3:2].C1C(=O)N([Br:33])C(=O)C1>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([Br:33])[C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([O:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1[Cl:25])[CH:10]=2)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 89813195HCID 89813195, compound

Product 1

HCID 89812883HCID 89812883, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-hydroxy-7-(4-fluoro-2-chloro-phenoxy)-isoquinoline-3-carboxylic acid ethyl ester (610 mg, 1.69 mmol) and NBS (331 mg, 1.86 mmol) in CH2Cl2 (17 mL) was refluxed for 3 h and then concentrated. Residue was triturate with acetone (15 mL). Solid was collected and dried to provide the title compound 540 mg (1.22 mmol) in 73% yield. 1H NMR (200 MHz) in CDCl3, δ ppm: 11.90 (s, 1H), 8.37 (d, J=8.8 Hz, 1H), 7.47 (m, 2H), 7.15 (m, 3H), 4.54 (br q, J=7.3 Hz, 2H), 1.49 (br t, J=7.3 Hz, 3H).

Workup

  1. temperaturewas refluxed for 3 h
  2. concentrationconcentrated
  3. customResidue was triturate with acetone (15 mL)
  4. customSolid was collected
  5. customdried

Sources & evidence

ORD record
ord-0d5fbf8e00e74995af6a01eb180c1df5
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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