Diethyl Ether → HCID 20323741, compound

HRID 839587Notes

Reaction equation

HRID 839587 reaction equation
[C:1]([N:3]1[CH2:8][C:7]2[C:9]3[C:18]([O:19][CH3:20])=[CH:17][C:16]([CH:21]([CH3:29])[CH:22]([CH3:28])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:15][C:10]=3[O:11][C:12]([CH3:14])([CH3:13])[C:6]=2[CH2:5][CH2:4]1)#[N:2].C[O-].[Na+].[Cl-].[NH4+].[CH2:35]([O:37]CC)C>CO>[CH3:13][C:12]1([CH3:14])[C:6]2[CH2:5][CH2:4][N:3]([C:1](=[NH:2])[O:37][CH3:35])[CH2:8][C:7]=2[C:9]2[C:18]([O:19][CH3:20])=[CH:17][C:16]([CH:21]([CH3:29])[CH:22]([CH3:28])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:15][C:10]=2[O:11]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 20323738HCID 20323738, compound

Product 1

HCID 20323741HCID 20323741, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 198 mg (0.5 mmole) of 2-cyano-5,5-dimethyl-8-(1,2-dimethylheptyl)-10-methoxy-1,2,3,4-tetrahydro-5H-[1]benzopyrano[3,4-d]pyridine and 2.7 mg (0.05 mmole) of sodium methoxide in 8 ml of methanol was refluxed with stirring for 3 hours and allowed to stir overnight at ambient temperature. Ammonium chloride (29.4 mg; 0.55 mmole) was added and the stirring was continued for an additional 2 hours. The reaction mixture was concentrated on a rotary evaporator to give a residue to which was added 1 ml of diethyl ether. The solid was collected by filtration to give 138 mg in two crops (59%) of methyl 5,5-dimethyl-8-(1,2-dimethylheptyl)-10-methoxy-1,2,3,4-tetrahydro-5H-[1]benzopyrano[3,4-d]pyridine-2-carboximidate as a light yellow solid, m.p. 134°-36° C. The ir and nmr spectra confirmed the structure.

Workup

  1. temperaturewas refluxed
  2. stirringto stir overnight at ambient temperature
  3. waitthe stirring was continued for an additional 2 hours
  4. concentrationThe reaction mixture was concentrated on a rotary evaporator
  5. customto give a residue to which
  6. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-b01d22a8b3794a55b67eddd834537343
Source dataset
uspto-grants-1978_06
Patent number
US04096265

Reaction notes

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