Hydroxylamine → (Z)-4-((5H-dibenzo[b,f]azepin-5-yl)methyl)-N-hydroxybenzamide

HRID 1946609Notes

Reaction equation

HRID 1946609 reaction equation
[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[N:6]([CH2:16][C:17]3[CH:26]=[CH:25][C:20]([C:21](OC)=[O:22])=[CH:19][CH:18]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[NH2:27][OH:28].[OH-].[Na+].C1COCC1>CO>[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[N:6]([CH2:16][C:17]3[CH:26]=[CH:25][C:20]([C:21]([NH:27][OH:28])=[O:22])=[CH:19][CH:18]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 787HydroxylamineHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59783517(Z)-methyl 4-((5H-dibenzo[b,f]azepin-5-yl)methyl)benzoate

Product 1

HCID 59783569(Z)-4-((5H-dibenzo[b,f]azepin-5-yl)methyl)-N-hydroxybenzamideYield 26%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Title compound 350 (147 mg, 0.43 mmol), hydroxylamine (50% in water, 6 mL) and sodium hydroxide (138 mg, 3.40 mmol) were stirred in methanol (3 mL) and THF (3 mL) at room temperature overnight. The organic solvent was evaporated and the precipitate was filtered off and washed with a little bit of cold methanol to afford title compound 351 (39 mg, 26%) as a yellow solid. 1H NMR (DMSO-d6) δ (ppm): 11.06 (s, 1H), 8.96 (s, 1H), 7.57 (d, J=8.4 Hz, 2H), 7.47 (d, J=8.4 Hz, 2H), 7.21 (td, J=1.6 and 7.2 Hz, 2H), 7.18-7.13 (m, 2H), 7.10 (dd, J=1.6 and 7.6 Hz, 2H), 6.6 (td, J=1.2 and 7.2 Hz, 2H), 6.85 (s, 2H), 5.00 (s, 2H). LRMS: 342.1 (calc) 343.2 (found)

Workup

  1. customat room temperature
  2. customovernight
  3. customThe organic solvent was evaporated
  4. filtrationthe precipitate was filtered off
  5. washwashed with a little bit of cold methanol

Sources & evidence

ORD record
ord-5490d78a71784d45a0be1c4d2cebdcf8
Source dataset
uspto-grants-2013_03
Patent number
US08399452B2

Reaction notes

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