Methanol → HCID 13362530, compound

HRID 464535Notes

Reaction equation

HRID 464535 reaction equation
C([O:4][CH:5]1[C:11]2[CH:12]=[N:13][CH:14]=[N:15][C:10]=2[C:9]2[CH:16]=[CH:17][C:18]([Cl:20])=[CH:19][C:8]=2[C:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[F:27])=[N:6]1)(=O)C.CO.[OH-].[Na+]>O1CCCC1>[Cl:20][C:18]1[CH:17]=[CH:16][C:9]2[C:10]3[N:15]=[CH:14][N:13]=[CH:12][C:11]=3[CH:5]([OH:4])[N:6]=[C:7]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])[C:8]=2[CH:19]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 13556939HCID 13556939, compound

Product 1

HCID 13362530HCID 13362530, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3.7 g (9.7 mmole) of 9-chloro-7-(2-fluorophenyl)-5H-pyrimido[5,4-d][2]benzazepin-5-ol acetate in a mixture of 25 ml of tetrahydrofuran, 50 ml of methanol and 2 ml of 3N sodium hydroxide was stirred at room temperature for 0.5 hr. The reaction mixture was poured into ice water and extracted with methylene chloride. The organic layer was seperated, dried over anhydrous sodium sulfate and concentrated in vacuo to dryness. The residue crystallized from a mixture of methylene chloride and ether to give a crude product melting at 186°-188° C. Recrystallization from a mixture of ether and methylene chloride gave the product as cream colored prisms, mp 196°-198° C.

Workup

  1. extractionextracted with methylene chloride
  2. customThe organic layer was seperated
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo to dryness
  5. customThe residue crystallized from a mixture of methylene chloride and ether

Sources & evidence

ORD record
ord-99f424259cb84464ac26980ea69b4da8
Source dataset
uspto-grants-1985_10
Patent number
US04547581

Reaction notes

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