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Hydroxylamine → 8-(2-(9H-fluoren-9-ylidene)acetamido)-N-hydroxyoctanamide

HRID 1926206
Notes
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Reaction equation

HRID 1926206 reaction equation
[CH:1]1[C:13]2[C:12](=[CH:14][C:15]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([OH:27])=O)=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.ClC(OCC)=O.[NH2:41][OH:42]>[Cl-].[Na+].O.CN(C=O)C>[CH:10]1[C:11]2[C:12](=[CH:14][C:15]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([NH:41][OH:42])=[O:27])=[O:16])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 787HydroxylamineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 579720638-(2-(9H-fluoren-9-ylidene)acetamido)octanoic acid

Product 1

HCID 445404368-(2-(9H-fluoren-9-ylidene)acetamido)-N-hydroxyoctanamideYield 44%

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

8-(2-(9H-fluoren-9-ylidene)acetamido)octanoic acid (363 mg, 1 mmol), triethylamine (151 mg, 1.5 mmol) and 20 ml of DMF were stirred at 0° C. while ethyl chloroformate (163 mg, 1.5 mmol) was added. The mixture was stirred at 0° C. for 2 hours, and then 50% aqueous solution of hydroxylamine (1.32 g, 20 mmol) was added. The mixture was stirred for 3 hours at room temperature, and then diluted with 1000 mL of brine. The solids were collected by vacuum filtration, washed with water and dried under vacuum to give the title compound (166 mg, 44%) as a yellow solid. LC-MS (m/z) 379 (M+1).

Workup

  1. additionwas added
  2. stirringThe mixture was stirred for 3 hours at room temperature
  3. filtrationThe solids were collected by vacuum filtration
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-00cc4f7b8a0b489091b7bad2cd7a5856
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08178577B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes