HCID 86600480, compound → HCID 11264804, compound

HRID 2105554Notes

Reaction equation

HRID 2105554 reaction equation
C([O:8][N:9]([CH2:12][CH:13]1[C:19](=[O:20])[NH:18][C:17]2[CH:21]=[CH:22][CH:23]=[CH:24][C:16]=2[CH2:15][CH2:14]1)[CH:10]=[O:11])C1C=CC=CC=1>CCO.[Pd]>[OH:8][N:9]([CH2:12][CH:13]1[C:19](=[O:20])[NH:18][C:17]2[CH:21]=[CH:22][CH:23]=[CH:24][C:16]=2[CH2:15][CH2:14]1)[CH:10]=[O:11]

Participants

4

Reactant 1

HCID 86600480HCID 86600480, compound

Product 1

HCID 11264804HCID 11264804, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of N-benzyloxy-N-(2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-ylmethyl)-formamide (0.052 mmol) and Pd/C (10%) (3 mg) in EtOH is degassed and filled with hydrogen. After the mixture is stirred at room temperature for 14 hours, Pd/C is removed by filtration. The filtrate is concentrated and purified by preparative thin layer chromatography (10% EtOH/CH2Cl2) to provide the title compound N-hydroxy-N-(2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-ylmethyl)-formamide. Yield: 58%. 1H NMR (400 MHz, MeOD): δ 8.13 (s, 1H), 7.87 (s, 1H), 7.17 (m, 2H), 7.06 (t, 1H, J=8.0 Hz), 6.92 (d, 1H, J=8.0 Hz), 3.88 (dd, 1H, J=8.0 Hz, J=14.4 Hz), 3.24 (dd, 1H, J=4.8 Hz, J=14.4 Hz), 2.77 (m, 2H), 2.62 (m, 1H), 2.11 (m, 1H), 1.84 (m, 1H). MS: (ES+): 235.2 [M+1].

Workup

  1. customis degassed
  2. additionfilled with hydrogen
  3. customPd/C is removed by filtration
  4. concentrationThe filtrate is concentrated
  5. custompurified by preparative thin layer chromatography (10% EtOH/CH2Cl2)

Sources & evidence

ORD record
ord-2874504e1182406ab1834bc7c4738bd7
Source dataset
uspto-grants-2009_08
Patent number
US07579363B2

Reaction notes

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