Ethyl chloroformate → HCID 57559687, compound

HRID 1723829Notes

Reaction equation

HRID 1723829 reaction equation
[NH2:1][C:2]1[C:3]([C:12]([OH:14])=[O:13])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.Cl[C:16]([O:18][CH2:19][CH3:20])=O>N1C=CC=CC=1>[CH2:19]([O:18][C:16]1[O:13][C:12](=[O:14])[C:3]2[CH:4]=[C:5]3[C:10]([CH:9]=[CH:8][CH:7]=[CH:6]3)=[CH:11][C:2]=2[N:1]=1)[CH3:20]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 222443-Amino-2-naphthoic acid

Product 1

HCID 57559687HCID 57559687, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-amino-2-naphthoic acid (3.74 g, 20.0 mmol, 1 equiv.) in pyridine (40 ml) at −10° C. under nitrogen was added ethyl chloroformate (7.6 ml, 8.63 g, 79.5 mmol, 4.0 equiv) dropwise over an hour. The reaction was stirred from −10° C. to room temperature over 20 hours. The solvent was evaporated under reduced pressure, water (100 ml) was added to the solid residue, and the mixture was stirred at room temperature for 1 hour. The precipitate was filtered, washed with water and dried to yield 2-ethoxy-4H-naphtho[2,3-d][1,3]oxazin-4-one (1-2) as a tan solid. LRMS m/z (M+H) 242.2 found, 242.1 required.

Workup

  1. customThe solvent was evaporated under reduced pressure, water (100 ml)
  2. additionwas added to the solid residue
  3. stirringthe mixture was stirred at room temperature for 1 hour
  4. filtrationThe precipitate was filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-2af20e43c7a74454bcc3949e983676b0
Source dataset
uspto-grants-2009_02
Patent number
US07485649B2

Reaction notes

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