Dichloromethane → Ammonium Hydroxide

HRID 1925352

Reaction equation

HRID 1925352 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]=1[OH:13])=[O:4].C(Cl)Cl>O>[NH4+:5].[OH-:4].[OH:12][C:9]1[CH:10]=[CH:11][C:6]2[NH:5][C:3](=[O:4])[CH2:2][O:13][C:7]=2[CH:8]=1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 529048732-chloro-N-(2,4-dihydroxyphenyl)acetamide

Product 2

HCID 14923Ammonium HydroxideHCID 100578707-hydroxy-3,4-dihydro-2H-1,4-benzoxazin-3-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-chloro-N-(2,4-dihydroxyphenyl)acetamide (20 g, 0.0995 mol) in CH2Cl2 (250 mL) sodium hydride (7.164 g, 0.2985 mol) was slowly added at RT. The resulting mixture was stirred for 6 h before water (10 mL) was slowly added. The solution was concentrated in vacuo and purified with column chromatography using 100% CH2Cl2→25%→40% 90:10:1 CH2Cl2:MeOH:NH4OH to yield the title compound. MS (ESI, pos. ion) m/z: 166 (M+1). Mass cal'd for C8H7NO3: 165.04.

Workup

  1. additionwas slowly added
  2. concentrationThe solution was concentrated in vacuo
  3. custompurified with column chromatography

Sources & evidence

ORD record
ord-ba0db010d25645a4b1a030b8f4409f51
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Linked notes

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