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Acetonitrile → 6-Cyano-1-dimethylcarbamoylmethoxycarbonyl-2-naphthol

HRID 1419257
Notes
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Reaction equation

HRID 1419257 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:13]([OH:15])=[O:14])=[C:8]([OH:16])[CH:7]=[CH:6]2)#[N:2].C(#N)C.[CH3:20][N:21]([CH3:26])[C:22]([CH2:24]Br)=[O:23]>C(N(CC)CC)C>[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:13]([O:15][CH2:24][C:22](=[O:23])[N:21]([CH3:26])[CH3:20])=[O:14])=[C:8]([OH:16])[CH:7]=[CH:6]2)#[N:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 2255442-Bromo-N,N-dimethylacetamideHCID 538463576-Cyano-1-carboxy-2-naphthol

Product 1

HCID 540823526-Cyano-1-dimethylcarbamoylmethoxycarbonyl-2-naphtholYield 78.5%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
70 °C

Procedure

To 28.4 g of 6-cyano-1-carboxy-2-naphthol were added 350 ml of acetonitrile, 18 ml of triethylamine and 33.2 g of dimethylcarbamoylmethyl bromide, followed by stirring for 24 hours at 70° C. and further 24 hours at room temperature. The resulting precipitate was collected by filtration and washed with water to obtain 31.2 g of the desired product.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with water

Sources & evidence

ORD record
ord-66aea4075ac74c379b3cd3eae13d178f
Source dataset
uspto-grants-1999_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05885990

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes