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Sodium Hydroxide → 3-(2-o-Tolylamino-benzoxazol-6-yl)propanoic acid

HRID 987528
Notes
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Reaction equation

HRID 987528 reaction equation
[C:1]1([CH3:24])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[O:9][C:10]2[CH:16]=[C:15]([CH2:17][CH2:18][C:19]([O:21]CC)=[O:20])[CH:14]=[CH:13][C:11]=2[N:12]=1.[OH-].[Na+]>CO>[C:1]1([CH3:24])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[O:9][C:10]2[CH:16]=[C:15]([CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH:14]=[CH:13][C:11]=2[N:12]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18008945Ethyl 3-(2-o-tolylamino-benzoxazol-6-yl)propanoate

Product 1

HCID 180089523-(2-o-Tolylamino-benzoxazol-6-yl)propanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A solution of ethyl 3-(2-o-tolylamino-benzoxazol-6-yl)propanoate (Reference Example 15) in methanol (50 ml) was treated with aqueous sodium hydroxide (5 ml, 1M). After stirring at 40° C. for 2 hours the mixture was evaporated to low volume and partitioned between ethyl acetate (50 ml) and water (50 ml). The aqueous phase was separated and acidified with aqueous hydrochloric acid (10 ml, 1M). The resulting precipitate was dried at 60° C. to give the title compound (1.1 g).

Workup

  1. customwas evaporated to low volume
  2. custompartitioned between ethyl acetate (50 ml) and water (50 ml)
  3. customThe aqueous phase was separated
  4. customThe resulting precipitate was dried at 60° C.

Sources & evidence

ORD record
ord-b38d8f145dad4f319171d8ce9861c74b
Source dataset
uspto-grants-2003_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06632814B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes