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Hydroxylamine → 6-(3-((5-fluoro-2-oxoindolin-3-ylidene)methyl)benzamido)-N-hydroxyhexanamide

HRID 251700
Notes
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Reaction equation

HRID 251700 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:12][C:13]1[CH:14]=[C:15]([CH:27]=[CH:28][CH:29]=1)[C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24](O)=[O:25])=[O:17].C(N(CC)CC)C.ClC(OCC)=O.[NH2:43][OH:44]>[Cl-].[Na+].O.CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:12][C:13]1[CH:14]=[C:15]([CH:27]=[CH:28][CH:29]=1)[C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([NH:43][OH:44])=[O:25])=[O:17]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 787HydroxylamineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 690325116-(3-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)benzamido)hexanoic acid

Product 1

HCID 766038976-(3-((5-fluoro-2-oxoindolin-3-ylidene)methyl)benzamido)-N-hydroxyhexanamideYield 41%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent
HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

6-(3-((5-fluoro-2-oxoindolin-3-ylidene)methyl)benzamido)hexanoic acid (396 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 (168 mg, 41%) as a brown solid. LC-MS (m/z) 412 (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-656c9f2bc79d4c118a23f618e9365f65
Source dataset
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07863315B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes