Ethyl chloroformate → HCID 57722727, compound

HRID 1986892Notes

Reaction equation

HRID 1986892 reaction equation
[NH2:1][C:2]1[C:3]([C:12]([OH:14])=[O:13])=[CH:4][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1.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]([CH2:9][CH2:8][CH2:7][CH2:6]3)=[CH:11][C:2]=2[N:1]=1)[CH3:20]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 137397303-Amino-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid

Product 1

HCID 57722727HCID 57722727, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-amino-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid (1-2) (5.0 g, 26 mmol, 1 equiv) in pyridine (50 mL) at −10° C. under nitrogen was added ethyl chloroformate (10 mL, 11 g, 100 mmol, 4.0 equiv) dropwise over 1 h. The resulting solution was stirred from −10° C. to 23° C. over 20 h. The solvent was evaporated under reduced pressure and the solid residue was suspended in water (100 mL) with stirring for 1 h. The precipitate was filtered, washed with water and dried to yield 2-ethoxy-6,7,8,9-tetrahydro-4H-naphtho[2,3-d][1,3]oxazin-4-one (1-3) as a yellow solid. LRMS m/z (M+H) 246.4 found, 246.1 required.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. stirringwith stirring for 1 h
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-a6496f29b52040e08db7fc1067d845b0
Source dataset
uspto-grants-2009_06
Patent number
US07550477B2

Reaction notes

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